Shadow

Arsenal, Chelsea, Liverpool, Man City, Man United, Tottenham

by Jacob Rodriguez


When looking back over 30 years of the Premier League, it might feel as though transfers between the Big Six — Arsenal, Chelsea, Liverpool, Manchester City, Manchester United, Tottenham Hotspur — are a rare occurrence, but they are not quite as rare as you might think.

Up to and including Oleksandr Zinchenko’s switch from Manchester City to Arsenal this summer, there have been a total of 80 moves directly from one of that clutch of teams to another since the league’s inception in 1992.

However, there has never been a single player to move directly between rivals Manchester United and Liverpool in all that time. In fact, you have to go all the way back to July 1964 to find the last senior professional player to do so, when Manchester-born forward Phil Chisnall left United after 13 seasons to join the Reds in a deal worth around £26,000.

Of course, the Big Six as we know it today has not always been that way: Chelsea were never title contenders before Roman Abramovich’s 2003 takeover, and City similarly were catapulted into the modern elite thanks to Sheikh Mansour’s investment in 2008. Tottenham, meanwhile, have yet to match the achievement of Leicester City or Blackburn Rovers by winning the title since it rebranded as the Premier League, so much of their current Big Six status is based on them being regular top-four finishers and Champions League participants over the past decade or so.

We’ve gone back and reviewed every single deal struck between clubs in what we now know as the Big Six — including loans and free transfers — since the summer of 1992 and ranked them by how successful they were.

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Let’s start with three signings that happened this summer, and are therefore ineligible to be ranked here:

Gabriel Jesus, Man City to Arsenal, July 2022, £46.9m

It’s far too early to assess Jesus’ transfer to Arsenal, but Gunners’ fans will be pleased the club have landed an experienced Premier League striker who provides more than just cute flourishes around the penalty area. With 95 goals in 236 games for City, Jesus is bound to add cut and thrust to an attacking line which has looked more than a little blunt in recent years. For their part, City have lost a talented player, albeit one who was often underused throughout his six-year stay at the Etihad, though now they have Erling Haaland to fill the void.

Raheem Sterling, Man City to Chelsea, July 2022, £47.5m

Again, we can’t judge Sterling’s impact at Chelsea yet, given he has only just arrived. But the England winger is only 27 and may not have even reached his peak yet, so it stands to reason that he will shine at Stamford Bridge. City’s wealth of options up front saw Sterling slip out of favour at the Etihad last season but, despite being left out of some of the club’s biggest games, he still chipped in with 17 goals in 47 games. City have almost certainly strengthened one of their rivals by allowing Chelsea to take a relatively young, highly adaptable, world-class forward off their hands for a decent fee as his contract was due to expire in 2023.

Oleksandr Zinchenko, Man City to Arsenal, July 2022, £30m

Zinchenko first moved to Man City in July 2016 as a promising 19-year-old midfielder but adapted to become a left-back and made most of his 128 appearances for the club there. While he hasn’t always been directly involved, he still won four Premier League titles, an FA Cup, four League Cups and reached the Champions League final, in which he played the entire game. Arsenal know they have still signed a seasoned player who is vastly experienced at international level. He is Ukraine’s youngest-ever goal scorer, beating the record previously held by superstar striker Andriy Shevchenko, and is also the youngest player to captain his country in an official competitive match.

Here are the other 77 players who have moved between the Premier League’s Big Six over the past three decades:

77. Frederic Veseli, Man City to Man United, January 2012, Free

After making waves by captaining Switzerland to glory at the 2009 Under-17 World Cup, defender Veseli was poached by City’s local rivals. He didn’t make a single senior appearance for United and left to join Ipswich Town on a free transfer just 18 months later.

76. Frode Grodas, Chelsea to Tottenham, January 1998, £315k

Grodas ended his debut season at Chelsea by playing in goal in the 1996-97 FA Cup final win, but then lost his place to Ed de Goey. The experienced Norway international left for Spurs but didn’t make a single appearance in six months there before joining Schalke that summer.

75. Tony Coton, Man City to Man United, January 1996, £518k

One of only three players to move directly between United and City during the Premier League era, Coton was a dependable goalkeeper who made more than 200 appearance in six years at Maine Road and precisely zero in a dismal six months at Old Trafford. He joined Sunderland in 1996, but he suffered a horrific multiple leg break that ended his career just a few months later. He’s made more of an impact at United since becoming the club’s chief goalkeeping scout in 2020.

74. Alexis Sanchez, Arsenal to Man United, January 2018, Swap

Sanchez became a Premier League star at Arsenal, scoring 80 goals from 166 games and finishing as top scorer with 30 in 2016-17. However, the collapse of a deadline-day transfer to Man City saw his form suffer a slow, jaded start to the 2017-18 campaign. Aware of his expiring contract, United engineered a midseason swap deal involving the equally out-of-sorts Henrikh Mkhitaryan. As one of the best-paid players in the world on a reported £350,000-a-week (£18m per year), the transfer proved to be a footballing and financial calamity, as Sanchez scored just three Premier League goals in 18 months. He was sent on loan to Inter Milan in August 2019 (with United still paying most of his wages) before waiving the final two years of his huge contract to join the Italian side on a free transfer. The signing was unveiled with his now-infamous piano performance, but it’s hard to think of a transfer that hit more of a bad note.

73. Mark Bosnich, Man United to Chelsea, January 2001, Free

The only player Ferguson ever signed twice for Manchester United. After establishing himself as a top goalkeeper with Aston Villa, Bosnich returned to Old Trafford in 1999 to succeed Peter Schmeichel. After issues with his fitness and conduct saw him sidelined. Bosnich joined Chelsea on a free but made just five league appearances before a failed drugs test brought a premature end to his Premier League career.

72. Paul Stewart, Tottenham to Liverpool, July 1992, £2.4m

A skillful, versatile attacking player, Liverpool signed Stewart as a direct replacement for striker Dean Saunders, who had left Anfield for Aston Villa. Unfortunately, injuries had a detrimental effect on Stewart’s progress and he scored just three goals in four years with the Reds before leaving for Sunderland in 1996.

71. Owen Hargreaves, Man United to Man City, August 2011, Free

Hargreaves was released by Manchester United at the end of the 2010-11 season after his four-year spell began with him winning the Champions League but became more akin to a rolling injury rehab clinic. United manager Sir Alex Ferguson even turned down the England international’s offer to play for free. Still, the midfielder posting his workout routines on YouTube was enough to convince City to take a gamble on his fitness for the 2011-12 campaign. Things went exactly as you’d expect, with Hargreaves making four appearances for Roberto Mancini’s side as they won their first historic Premier League title. He didn’t qualify for a medal, and he was released that summer.

70. Jason Cundy, Chelsea to Tottenham, July 1992, £788k

After spending the latter part of the 1991-92 season on loan at Tottenham in the old First Division, Cundy impressed sufficiently for Spurs to sign the tough centre-back on a permanent deal for the inaugural Premier League campaign. Cundy started just 15 league games in his four years at Spurs. Now better known as a brash presence on sports radio.

69. Robbie Keane, Tottenham to Liverpool, July 2008, £21.6m

Keane was a force of nature in his first six seasons at Tottenham, scoring 107 goals in 254 games and winning the club’s Player of the Year award three times. The 28-year-old joined Liverpool despite an official complaint from Spurs over the manner in which the approach was made, but what was supposed to be a dream move quickly became an unmitigated disaster. His incredibly brief Anfield career lasted just half a season, as Keane struggled with coach Rafa Benitez’s insistence that he play off Fernando Torres rather than as a main striker. Keane scored five goals in 19 appearances before being hurriedly moved back to Tottenham, just 189 days after leaving. The loss Liverpool took on the deal meant Keane cost them £1m a month.

68. Terry Phelan, Man City to Chelsea, November 1995, Nominal fee

A First Division and Premier League staple for many years, Phelan enjoyed success at Wimbledon and City, for whom he made well over 100 appearances. The Republic of Ireland international failed to make an impact in an unremarkable two-year stint at Stamford Bridge before opting to sign for Joe Royle’s Everton in 1997.

67. David Rocastle, Man City to Chelsea, August 1994, £1.3m

The late midfielder is rightly regarded as a legend at Arsenal, though “Rocky” also had his moments during subsequent stints at Leeds and Manchester City despite a recurring knee injury limiting his involvement. It was at Chelsea that those problems really took their toll — the winger played just one game across the entire 1995-96 season. Mediocre loans at Hull City and Norwich City followed as Rocastle remained on the Blues’ books until his contract expired in the summer of 1998. His untimely death from cancer at the age of 33 came just three years later.

66. Rohan Ricketts, Arsenal to Tottenham, July 2002, Free

A true journeyman, Ricketts played for 19 clubs in 11 different countries. The Arsenal youth prospect made headlines when he became only the fourth Gunner ever to move directly to Tottenham. After taking a full year to make his first-team debut, Ricketts made 28 appearances in 2003-04, but that promising start fizzled out into a long period of miscellaneous loans and globe-trotting free transfers that took him as far afield as Canada, Moldova, Ecuador, Thailand and Bangladesh. An early adopter of Twitter, Ricketts used the social media platform to keep fans updated on his nomadic career.

65. Lassana Diarra, Chelsea to Arsenal, August 2007, £2.6m

The beginning of Diarra’s rather uneven transfer progression that took him from Chelsea to Arsenal to Portsmouth to Real Madrid. The France international midfielder won back-to-back FA Cups with Chelsea (2006-07) and Portsmouth (2007-08) with a forgettable five-month spell at the Emirates sandwiched in the middle.

64. Eddie McGoldrick, Arsenal to Man City, September 1996, £405k

McGoldrick made 38 Premier League appearances for Arsenal before dropping down a rung to sign for Man City, then of the (second tier) First Division (now the Championship). The midfielder was the only permanent signing during Steve Coppell’s infamous 32-day tenure in charge of City, and he played under four different managers during his first turbulent season at Maine Road.

63. Mal Donaghy, Man United to Chelsea, July 1992, £180k

Northern Ireland international Donaghy holds the distinction of being the first player to transfer between two of the modern-day Big Six in the Premier League era. The veteran defender joined Chelsea after four years with United and was a regular at Stamford Bridge for two years before retiring in his late 30s.

62. Neil Sullivan, Tottenham to Chelsea, July 2003, Free

Sullivan joined Chelsea as cover for Carlo Cudicini — an arrangement that lasted until the 2005 when Petr Cech arrived on the scene at Stamford Bridge. Sullivan’s recruitment at the age of 33 was a forerunner of the current practice of top clubs hiring experienced, older goalkeepers to train alongside their No. 1s.

61. Nigel Clough, Liverpool to Man City, January 1996, £1.5m

Clough was Nottingham Forest’s top scorer as they were relegated from the Premier League in its inaugural season. Liverpool paid £2.25m to sign the forward, but he soon lost his place to teenage sensation Robbie Fowler. In 1996 he joined strugglers City in a midseason transfer, but he couldn’t help them avoid the drop. Two injury-riddled years at Maine Road followed before Clough joined non-league Burton Albion, where he began a respectable career as a lower-league manager with a knack for cup runs and upsets.

60. Fraizer Campbell, Man United to Tottenham, September 2008, Loan

After coming through United’s academy, Campbell was on the brink of the first-team squad but was sent on loan to Royal Antwerp and Hull City. A third successive loan was agreed as the striker joined Tottenham for the 2008-09 season as part of the deal that saw Dimitar Berbatov go the other way. However, Campbell struggled and ended the campaign with just one goal in 11 Premier League appearances. Aged 21, he left for Sunderland in the summer of 2009 on a permanent deal, having made four senior appearances for United, the club he joined as a schoolboy.

59. Joe Cole, Chelsea to Liverpool, July 2010, Free

Seen as a generational English talent akin to Paul Gascoigne, Cole joined Chelsea from boyhood club West Ham for £6.6m in 2003 as one of Abramovich’s first wave of signings. Seven years and three league titles later, he left after failing to agree a new contract. The 28-year-old was snapped up by Liverpool on a free transfer and immediately handed the No. 10 shirt. However, despite the misguided public assertion from club captain Steven Gerrard that Cole was as good as Lionel Messi, he failed to click at Anfield. He scored five goals in 42 games for the Reds and spent the 2011-12 season on loan at Lille before rejoining West Ham in January 2013.

58. Willian, Chelsea to Arsenal, August 2020, Free

Willian scored 61 goals in 337 games over seven years at Chelsea while winning two Premier League titles, an FA Cup, a League Cup and the Europa League. After registering his highest league goal tally in a Chelsea shirt (nine goals) in 2019-20, the Brazilian failed to agree a new contract and signed for the Gunners on a three-year deal worth £100,000 a week. Despite registering three assists on his debut for the club, the awkward relationship lasted just one season before the 33-year-old was released by mutual consent in order to re-sign for boyhood club Corinthians, though he has now departed from there as well.

57. Ronny Rosenthal, Liverpool to Tottenham, January 1994, £270k

Rosenthal suffers the misfortune of being largely remembered for his diabolical miss in front of an open goal against Aston Villa in 1992-93. The Israel striker’s reputation never really recovered, and after falling behind Iran Rush, new signing Nigel Clough and breakthrough star Robbie Fowler at Anfield, he left for Tottenham. He scored just eight goals in 94 games for Spurs, although that included a memorable hat trick in a 6-2 win at Southampton in an FA Cup fifth-round replay.

56. Yossi Benayoun, Liverpool to Chelsea, July 2010, £6.3m

Benayoun proved his ability as a creative attacking midfielder in the Premier League at West Ham and Liverpool only to run out of steam at Chelsea, where he made just 14 appearances in three years — the final two of which he spent out on loan at Arsenal and former club West Ham.

55. Neil Ruddock, Tottenham to Liverpool, July 1993, £2.7m

A decent if rugged centre-back in his day, “Razor” was an archetypal hardman who felt like a footballing anachronism even in the early to mid-1990s. Still, he lasted five years at Anfield, winning the League Cup in 1994-95. He is now a TV personality, which was perhaps his true calling all along.

54. Carlo Cudicini, Chelsea to Tottenham, January 2009, Free

The talented goalkeeper spent several seasons as Chelsea No. 1 before the arrival of Cech in 2004-05 saw him demoted overnight. The Italian spent the next four years as a sub until Tottenham gave him the chance to re-establish himself. However, he was soon back on the bench as Heurelho Gomes and later Brad Friedel usurped him. He made 37 appearances in five years at White Hart Lane before finishing his career at LA Galaxy in MLS.

53. Juan Sebastian Veron, Man United to Chelsea, August 2003, £19.6m

Regularly cited as one of the biggest transfer flops in Premier League history, Veron’s £28m move to Manchester United from Lazio in 2001 was the most expensive transfer ever in English football at the time. Exquisite as he might have been, the Argentina midfielder underwhelmed as repeated injuries and an inability to settle into the Premier League made him look very ordinary. But with Abramovich’s arrival in 2003, Chelsea took a chance on Veron. He showed signs of rejuvenation before succumbing to yet more injury woes, and he spent the final two years out on loan with Inter Milan and Estudiantes respectively. He made just 14 appearances for the Blues before finally completing a permanent return to Estudiantes in 2007.

52. John Scales, Liverpool to Tottenham, December 1996, £2.7m

A refined centre-back, Scales was a stalwart for Wimbledon in the pre-Premier League era and earned a big move to Liverpool — the team “The Crazy Gang” famously beat in the final of the 1988 FA Cup — at the start of the 1993-94 season. After playing his way into the England set-up, Scales moved back to London to sign for Tottenham but failed to gain a foothold in the team due to fluctuating form and injuries. He made a couple more Premier League appearances for Ipswich Town before retiring.

51. Oyvind Leonhardsen, Liverpool to Tottenham, July 1999, £4m

Leonhardsen was ousted from the Liverpool first team upon the arrival of manager Gerard Houllier in 1998. The Norway international winger joined Tottenham to play alongside fellow Scandinavians Steffen Iversen and Allan Nielsen. Leonhardsen played regularly under George Graham only to lose his starting place when club legend Glenn Hoddle took over. He scored 10 goals in 69 games for Spurs before moving to Aston Villa on a free transfer for the 2002-03 season.

50. Christian Ziege, Liverpool to Tottenham, July 2001, £5.8m

The Germany international won a treble (League Cup, FA Cup, UEFA Cup) during his sole season at Anfield, but made only 16 league appearances due to a mix of injuries and wavering form. Tottenham then signed him and he scored the equaliser in the 2002 League Cup final as Spurs lost 2-1 to Blackburn. However, the wing-back continued to be hampered by persistent knee and ankle issues and eventually saw his Spurs contract cancelled by mutual consent in the summer of 2004. He returned home to Germany and signed for Borussia Monchengladbach but managed only one Bundesliga appearance for the club before retiring aged 33.

49. Victor Moses, Chelsea to Liverpool, September 2013, Loan

A brief stop in an intriguingly diverse career, Liverpool were the first of six clubs the versatile Nigeria international found himself loaned to during his nine years on the books at Stamford Bridge. However, in the midst of all that, he played a pivotal role for then-coach Antonio Conte, who converted Moses into a wing-back in a 3-4-3 formation that powered the Blues to the Premier League title in 2016-17.

48. David Seaman, Arsenal to Man City, July 2003, Free

An Arsenal legend, having played more than any other goalkeeper in the club’s history, Seaman ended his glorious 13-year stint at the Gunners at the age of 39 after lifting the FA Cup for the fourth time. He arrived at City after veteran Schmeichel retired, but he only played another 19 times in the Premier League before a shoulder injury forced him to quit in January 2004.

47. Robbie Fowler, Man City to Liverpool, January 2006, Free

Fowler is still the eighth-highest scorer in Premier League history with 163 goals to his credit, 128 of which were scored in 266 games for boyhood club Liverpool. The striker left for Leeds United in an £11m deal in 2001, but injury problems and persistent fitness issues, coupled with Leeds’ spiralling debts, led to him signing for Man City. However, Fowler fell out of contention to the point that City let him rejoin Liverpool on a free transfer. The return did coincide with a minor uptick in 30-year-old’s productivity as he scored nine goals in 21 appearances. Fowler ended the 2006-07 season with a Champions League runners-up medal, despite not being named in the matchday squad for the defeat against AC Milan in the final, and left the club for Cardiff City a few weeks later.

46. Jamie Redknapp, Liverpool to Tottenham, April 2002, Free

Redknapp made his name as a ball-playing midfielder at Liverpool, and his career peaked under Roy Evans in the mid-1990s — encompassing the infamous “Spice Boys” era. With injuries already beginning to disrupt his playing time at the age of 28, Redknapp ended his 11-year stint at Anfield by joining Spurs. He played 49 times and scored four goals in 2½ injury-ravaged years at White Hart Lane before being released in January 2005. Jamie then became father Harry Redknapp’s first signing as Southampton manager mere days later, making 16 league appearances for the club before retiring.

45. Daniel Sturridge, Man City to Chelsea, July 2009, £6.5m

After being named Man City’s 2008-09 Young Player of the Year, academy graduate Sturridge signed for Chelsea on a four-year deal. Unfortunately, the ambitious 19-year-old striker found himself behind Didier Drogba, and a lack of first-team action led to him joining Bolton for the latter half of the 2010-11 season. Sturridge scored 24 goals in 96 games over four years at Chelsea without ever managing to cement his place — though he did win the Premier League, two FA Cups and the Champions League. Aged 23 and still seeking game time in his preferred central No. 9 role, the forward signed for Liverpool in January the following season.

44. Yossi Benayoun, Chelsea to Arsenal, August 2011, Loan

Finding opportunities scarce at Chelsea, Benayoun signed for Arsenal on a season-long loan for the 2011-12 campaign. The Israel international midfielder played 25 games, scored six goals and created three assists during his short run with the Gunners. A decent return, but few would remember his stint at the club unprompted.

43. Shaun Wright-Phillips, Chelsea to Man City, August 2008, £10.1m

Wright-Phillips came to prominence at Man City as an energetic young winger with an eye for a wonder goal. However, after a £21m move to Chelsea in 2005, the England international found himself on the fringes, and a return to his old club didn’t change that. Despite scoring twice on his second debut, he was soon shunted on to the bench when City began to flex their new financial clout by bringing in big names like Yaya Toure and David Silva.

42. Fernando Torres, Liverpool to Chelsea, January 2011, £52.6m

During his Liverpool pomp, Torres ranked among the most prolific strikers the Premier League has ever seen, scoring 80 goals in 141 games and even finishing third in the 2008 Ballon d’Or vote. But a British-record move to Chelsea coincided with a huge plateau in his fitness, form and confidence. While his work rate and attitude couldn’t be faulted, it still took 900 minutes of action for Torres to score his first goal for the Blues. “El Nino” was in and out of the starting XI but, despite his productivity tapering off, he still managed to play a vital role in Chelsea’s run to glory in the 2011-12 Champions League, scoring a famous tie-sealing breakaway goal against Barca in the semifinals. Taken in isolation, Torres’ numbers for Chelsea (45 goals in 171 games) weren’t an embarrassment, but his notorious open-goal miss at Old Trafford in 2011 was (despite having already scored in that game).

41. Bacary Sagna, Arsenal to Man City, July 2014, Free

Sagna signed for Man City as a 31-year-old free agent after he ran down his Arsenal contract just after winning the FA Cup, the first trophy of his seven-year spell with the Gunners. If the France international had arrived expecting to add a lot more silverware to his collection, things didn’t work out that way; he left for Italian club Benevento three years later with just a 2015-16 League Cup winners medal to his name.

40. Tal Ben Haim, Chelsea to Man City, July 2008, £5.76m

Ben Haim was a dependable, experienced centre-back who was signed by City to bolster their defensive ranks. Aged 26 at the time, the Israel international spent just one season with Chelsea but failed to oust John Terry, Ricardo Carvalho and Alex from the first team, making just 13 Premier League appearances. He continued to spend a lot of time on the City bench under Mark Hughes, ending his first season on loan at Sunderland. Upon his return, it was clear that the defender was already deemed surplus to requirements, and City agreed to release him after just 12 months, freeing him up to join Portsmouth.

39. Mikael Silvestre, Man United to Arsenal, August 2008, £855k

Silvestre made 249 Premier League appearances and won four titles in his nine years at Old Trafford. Premier League rivals Arsenal then surprisingly signed the 31-year-old France international after he’d missed much of the 2007-08 season with a knee ligament injury. He lasted two seasons at the Emirates but played only 26 times in the Premier League before being released in July 2010.

38. Shaun Wright-Phillips, Man City to Chelsea, July 2005, £28.3m

Wright-Phillips was supposed to kick on at Chelsea after showcasing his potential at Man City, regularly lighting up the league with his ferocious pace and style out on the flanks. Unfortunately, the England international was used as a squad player, with the likes of Arjen Robben, Damien Duff, Joe Cole and Florent Malouda regularly preferred. SWP returned to City after three years to little fanfare.

37. Henrikh Mkhitaryan, Man United to Arsenal, January 2018, Swap

One of many players who fell foul of Jose Mourinho during his tempestuous reign, Mkhitaryan found himself adrift at Old Trafford. But an escape route presented itself when the Armenia forward was included in a rare straight swap deal with Arsenal’s Sanchez. While Sanchez flopped, Mkhitaryan fared a little more favourably and scored nine goals in 59 games before leaving to join Roma in 2019, first on loan and then on a permanent basis. Mourinho turned up as Roma coach in 2021, and Mkhitaryan is now at Inter Milan.

36. David Luiz, Chelsea to Arsenal, August 2019, £7.8m

Luiz first joined Chelsea in January 2011 and won the Champions League and Europa League in consecutive seasons before being transferred to Paris Saint-Germain in the summer of 2014 for a fee of around £50m — a world record for a defender. The Brazil international then returned to Chelsea in August 2016 and spent a further three years at Stamford Bridge before moving across London to sign for rivals Arsenal as a 34-year-old. Luiz endured an erratic two seasons with the Gunners in which he indulged his penchant for conceding penalties, committing errors and attracting cards with alarming regularity. There were also high points amid all the haphazard slapstick, including being selected to play in the 2019-20 FA Cup final win over Chelsea and being involved in one of the most meta moments in football history. Luiz made just 20 Premier League appearances in his second season at the Emirates before returning to Brazil with Flamengo.

35. Craig Bellamy, Man City to Liverpool, August 2011, Free

Having first played for Liverpool in 2006-07 — scoring in a famous Champions League win at Barcelona — Bellamy returned after three seasons at City. The volatile Wales striker had found minutes increasingly hard to come by as City’s spending continued to spiral. After a loan spell at Cardiff, his tried his luck back at Anfield. Bellamy lasted just one season, scoring nine goals in 39 games, though most of his appearances came off the bench. He then went back to Cardiff and was part of a Bluebirds team that won promotion from the Championship that year.

34. Willy Caballero, Man City to Chelsea, July 2017, Free

Caballero signed for Chelsea in the summer of 2014 but made just 37 appearances in three years before he moved to Premier League champions Man City. Largely serving as an able deputy, and making just 11 Premier League appearances in four years, the Argentina international filled in when required and never really put a foot wrong while doing so.

33. Robbie Keane, Liverpool to Tottenham, February 2009, £15m

Tottenham were more than happy to re-sign Keane from Liverpool after just six months at Anfield, and the Republic of Ireland striker soon found his feet once again, though his numbers did begin to tail off. Keane scored 15 goals in 52 games in his second spell at White Hart Lane, which also took in loan spells at Celtic (2009-10) and West Ham (2010-11), before making a fresh start with LA Galaxy, where he won three MLS Cups alongside David Beckham and Landon Donovan.

32. Emmanuel Adebayor, Arsenal to Man City, July 2009, £26.1m

Adebayor scored 62 goals in 142 games at Arsenal to cement his reputation as one of the most prolific, if unpredictable, strikers in the Premier League. But the Togo international’s relationship with the Gunners’ fans became frayed after criticism over his perceived lack of commitment. He moved to Man City and netted 14 goals in his debut season, though the defining moment came in September when he sprinted the entire length of the pitch to celebrate in front of the away fans, almost sparking a mass pitch invasion in the process, after scoring against his former team. The striker spent the majority of his three seasons at City out on loan (with Real Madrid and Tottenham) after latterly falling below Carlos Tevez, Edin Dzeko and Mario Balotelli in the pecking order.

31. William Gallas, Arsenal to Tottenham, August 2010, Free

Only three male players have moved between Arsenal and Tottenham since the start of the Premier League, and former Gunners captain Gallas is the most recent to do so. The outspoken France defender signed a one-year contract with Spurs after being released by Arsenal and played well enough in the club’s first Champions League campaign to earn another two-year deal. However, Gallas then succumbed to numerous injuries and made only 20 further league appearances before being released at the end of the 2012-13 campaign. He then spent one year in the A-League with Perth Glory before retiring.

30. Emmanuel Adebayor, Man City to Tottenham, Aug 2012, £5.7m

After finishing as Tottenham’s top scorer with 18 goals in his initial loan season at the club, Adebayor’s output fell dramatically after the move was made permanent, with eight in 34 games the following campaign. Overall, the striker scored 24 goals in 76 games in his three seasons as a permanent Spurs player, including just two in 17 appearances in all competitions in his final year at White Hart Lane (2014-15).

29. Paul Dickov, Arsenal to Man City, July 1996, £1.3m

Chances at Arsenal were limited in the early 1990s, so Dickov made the move to third-tier City. He scored 43 goals for the club across two stints (1996-2002; 2006-2008), but one stands head and shoulders above the rest: his 95th-minute equaliser in the 1999 Division Two playoff final against Gillingham that hauled City back from the brink and forced the tie into extra time. City won the game on penalties and clinched promotion to Division One, beginning their ascent back up to the Premier League and everything that followed.

28. Mark Hughes, Man United to Chelsea, July 1995, £1.7m

Chelsea were far from the Premier League powerhouse they are today when Man United’s superstar striker swapped Old Trafford for Stamford Bridge. Aged 32, it was hoped that Hughes’ addition would see Chelsea progress from an unremarkable 11th-place finish in 1994-95. The Wales international scored nine league goals in his debut season but was unable to elevate Chelsea any further. Yet a sudden influx of foreign talent proved the catalyst required as Hughes was joined by world-renowned stars such as Ruud Gullit, Gianluca Vialli and Gianfranco Zola, all of whom combined beautifully to deliver the Blues’ first major silverware in 16 years: the 1996-97 FA Cup.

27. Kolo Toure, Man City to Liverpool, July 2013, Free

Toure won titles with both Arsenal and Man City, and came close to becoming the first player to win the Premier League at three different clubs with his move to Anfield. The Ivory Coast centre-back only played 18 games for City in his final season and found himself left out of the club’s Champions League squad, but Liverpool boss Brendan Rodgers wanted cover for the retiring Jamie Carragher. Toure made 70 appearances in three seasons at Anfield — the first of which saw the Reds come agonisingly close to becoming champions.

26. Nemanja Matic, Chelsea to Man United, July 2017, £40.2m

After impressing in his second stint at Chelsea, Matic was brought to Manchester United by his former manager at Stamford Bridge: Mourinho. Physically imposing and almost impossible to shake off the ball, the defensive midfielder made 188 appearances for United, though was never able to win a trophy, with the closest he came being runners-up medals in both the 2017-18 FA Cup and the 2020-21 Europa League. Aged 33 and finding game time increasingly scarce, the Serbia international announced that his fifth season at United would be his last. He has since signed for AS Roma, who just happen to be coached by Mourinho.

25. Gus Poyet, Chelsea to Tottenham, July 2001, £3m

Poyet established himself as a gritty-yet-skillful midfielder with the propensity to score outlandish goals during his three years at Chelsea. However, the arrival of a 22-year-old Frank Lampard at Stamford Bridge saw that 33-year-year-old Uruguayan shipped out to Spurs (in the same window as coach Glenn Hoddle also re-signed Sheringham at the age of 35.) Poyet scored 14 goals in 43 games in his debut season at White Hart Lane as Spurs reached the League Cup final, but the next two years were hampered by injuries before he hung up his boots in 2004.

24. Alex Oxlade-Chamberlain, Arsenal to Liverpool, August 2017, £34.2m

Oxlade-Chamberlain has the distinction of being the only player to have transferred between Arsenal and Liverpool (or vice-versa) in the Premier League era, with his move the first since midfielder Michael Thomas made his switch in December 1991 in a deal worth around £200,000. Brought in by Jurgen Klopp as a versatile midfield option, Oxlade-Chamberlain has endured a patchy few years at Anfield with recurring injury problems making it difficult for him to establish any kind of rhythm. That said, he has still played 133 times, scored 17 goals and won both the Champions League and the Premier League in his four seasons on Merseyside.

23. Danny Welbeck, Man United to Arsenal, September 2014, £18m

Welbeck joined Manchester United’s academy at age 8 and went on to score 29 goals in 142 appearances for his boyhood side. He was only 23 when he joined Arsenal on transfer deadline day in 2014-15 but, after a promising start at the Emirates, familiar injury woes returned to blight Welbeck’s progress. However, he remained popular with Arsenal fans over the course of his five years there, not least for scoring the goal that defeated United in front of a stunned Old Trafford crowd in a 2014-15 FA Cup campaign that ended with the Gunners lifting the trophy.

22. Daniel Sturridge, Chelsea to Liverpool, January 2013, £13.5m

Stuck behind Drogba in the pecking order at Chelsea, Sturridge got the chance to deliver on his potential at Anfield. The striker spent seven seasons at Liverpool and scored 68 goals in 160 games, but recurring injuries derailed him again and again just as he was beginning to hit his stride. He was part of Liverpool’s Champions League-winning side of 2018-19 but played only nine minutes beyond the group stage before spending the final on the bench.

21. Teddy Sheringham, Man United to Tottenham, July 2001, Free

After quenching his thirst for silverware at Man United, the 35-year-old Sheringham snubbed a contract extension and returned to Tottenham as the reigning PFA Players’ Player of the Year and FWA Footballer of the Year. The forward added another 26 goals to his Spurs tally in his second stint at the club before his two-year deal expired and he joined newly promoted Portsmouth at age 37. Impressive enough, but he still wasn’t done: a three-year spell at West Ham followed, during which he became, and remains, the oldest outfield player to score (40 years and 268 days) and appear (40 years, 272 days) in the Premier League.

20. Vedran Corluka, Man City to Tottenham, September 2008, £12.3m

Corluka left City after just one season, handing in a transfer request to join close friend and Croatia international teammate Luka Modric at Tottenham. The versatile defender was a mainstay in his first three seasons at White Hart Lane — including eight appearances in Spurs’ maiden Champions League campaign in 2010-11 — but the emergence of Kyle Walker spelled the end for Corluka, and he joined Lokomotiv Moscow in 2012.

19. Juan Mata, Chelsea to Man United, January 2014, £40.2m

After being a key player during his first three years at Chelsea, Mata was allowed to leave midway through the 2013-14 season having been consigned to the bench by returning manager Mourinho. Manchester United jumped at the chance to sign the Spain international in what was then a club-record deal and Mata instantly started repaying the faith, chipping in with 16 goals in his first 50 games for the Red Devils. Mata remained a faithful, cheerful, optimistic servant at Old Trafford for nine years, despite the club’s recent struggles. He scored 51 goals and clocked up 47 assists over 285 appearances, winning an FA Cup, League Cup and Europa League before being released as a 34-year-old this summer.

18. Kolo Toure, Arsenal to Man City, July 2009, £16.8m

Toure was already a Premier League champion when he joined City, having been Sol Campbell’s defensive partner during Arsenal’s “Invincibles” season of 2003-04. He was the club’s sixth signing of a hectic summer window as the club took the fast track to the top four, and he made 14 appearances in their maiden title-winning campaign of 2011-12. A year after Kolo joined, his brother Yaya also came to City, and the pair’s time together at the club inspired one of the most memorable football chants of modern times.

17. Raul Meireles, Liverpool to Chelsea, Aug 2011, £12.1m

After just one season at Liverpool, Meireles handed in a shock transfer request in order to speed up a move to Chelsea. The Portugal midfielder’s reunion with former Porto coach Andre Villas-Boas at Stamford Bridge lasted only until March, when Villas-Boas was sacked and replaced by interim boss Roberto Di Matteo. A few months later, Meireles was an FA Cup and Champions League winner but then moved clubs again in the summer, this time to Turkish side Fenerbahce.

16. Samir Nasri, Arsenal to Man City, August 2011, £24.7m

Nasri excelled with the ball at his feet, scoring 27 goals and laying on 15 assists in 126 games with Arsenal. But the France midfielder’s relationship with the fans soured, and he chose to goad them by saying he was looking forward to finally playing for a club with “more passionate” fans when he arrived at City. Nasri played a significant role for the club over next three seasons, before an injury hit 2015-16 saw him slide out of contention. After a season-long loan at Sevilla in 2016-17, he moved to Turkish side Antalyaspor before being given a six-month doping ban by UEFA in 2018.

15. Emmanuel Adebayor, Man City to Tottenham, August 2011, Loan

When the arrival of Sergio Aguero pushed Adebayor even further down the pecking order of strikers at City, the ex-Arsenal player found salvation from an unlikely source. The Togo striker had scored eight goals for the Gunners against Spurs, so he had his work cut out in winning his new fans over. But win them over he did, scoring 18 goals in 37 games to finish as the club’s top scorer. That earned him a permanent move the following summer, but he scored only another 24 times for Spurs in three-and-a-half years before he was allowed to join Crystal Palace in a midseason free transfer.

14. Wayne Bridge, Chelsea to Man City, January 2009, £11.7m

Bridge was among City’s first influx of big-money signings following the completion of Abu Dhabi United Group’s takeover. The England left-back made a solid start to his City career, but things soon began to unravel off the pitch amid newspaper allegations regarding his former girlfriend and ex-teammate John Terry — which led to the memorable moment when he refused the England captain’s prematch handshake. City then signed two new left-backs — Aleksandar Kolarov and Gael Clichy — in less than a year, rendering Bridge surplus to requirements. Loans to West Ham, Sunderland and Brighton came and went before the 32-year-old left the Etihad in June 2013, signing for Championship side Reading.

13. Gael Clichy, Arsenal to Man City, July 2011, £7m

Another international full-back who traded Arsenal for City at the turn of the 2010s, Clichy was signed as competition for Kolarov and immediately established himself as first choice. Winning two Premier League titles and two League Cups, Clichy remained at the Etihad until May 2017, when he joined Turkish Super Lig side Istanbul Basaksehir.

12. William Gallas, Chelsea to Arsenal, August 2006, Free

Gallas spent five years at Chelsea and was among the best centre-backs in the Premier League at the time. However things turned sour towards the end amid a feud with manager Mourinho, when the defender refused to sign a new contract. He eventually agreed to be included as a makeweight in the protracted and highly fractious deal with Arsenal for left-back Ashley Cole. Bizarrely handed the No. 10 shirt vacated by recently retired striker Dennis Bergkamp, Gallas did a decent job for the Gunners, playing 142 games and even scoring 17 goals, as he was made captain. Old obnoxious habits also surfaced from time to time, with his infamous “sit-down” at the end of a game against Birmingham City blotting his record somewhat. Four seasons at Arsenal came to an end in familiar fashion when the rejection of another contract saw Gallas sign for local rivals Tottenham on a one-year deal.

11. Petr Cech, Chelsea to Arsenal, July 2015, £12.6m

One of the greatest goalkeepers of his era, Cech won four Premier League titles, four FA Cups, three League Cups, the Champions League and the Europa League in 11 years at Stamford Bridge. However, after making only seven league appearances in 2014-15 as he lost his place to Thibaut Courtois, the 33-year-old 400-game veteran joined Arsenal. In four years at the Emirates, the Czech Republic international won another FA Cup and kept 54 clean sheets in 139 games for the club. His playing career ended in rather unbefitting fashion, as his final professional appearance came in Arsenal’s dismal 4-1 defeat to Chelsea in the 2019 Europa League final, but just a few weeks later he returned to Stamford Bridge as a technical and performance advisor, a position he held for three years until he left this summer.

10. Olivier Giroud, Arsenal to Chelsea, January 2018, £15.3m

One of the most underrated strikers of his generation despite being a World Cup winner, Giroud won three FA Cups and scored 105 goals in 253 games, thus making him the club’s sixth all-time highest goal scorer. Having made just one league start in the 2017-18 season, he moved to Chelsea and, though he continued to be deployed as a “Plan B” option, added to his enviable trophy haul with an FA Cup, Champions League title and the Europa League title (for which he “thanked” former club Arsenal after beating them in the final.) The veteran also set a number of individual scoring records during his time at Chelsea, becoming the oldest player to score a Champions League hat trick (by scoring all four goals in a 4-0 win over Sevilla) as well as the oldest player to score in six successive Premier League starts. Giroud brought his time at Chelsea to an end after serving as an unused substitute in the 2020-21 Champions League final, before joining AC Milan.

9. Dimitar Berbatov, Tottenham to Man United, September 2008, £34.2m

Berbatov routinely dazzled during his two years at Tottenham with his languid style and expert ball control as well as his goals. But when United lodged an interest in signing the Bulgaria striker, Tottenham alleged their “arrogant” Premier League counterparts were attempting to deliberately unsettle him. Sure enough, questions over his focus saw Berbatov left out of Juande Ramos’ squad for the first two fixtures of the 2008-09 season before Spurs finally accepted a late bid on deadline day that was a British record for about an hour until Man City’s new owners signed Robinho. Berbatov was a slow burner at Old Trafford yet he still won the Premier League, League Cup and FIFA Club World Cup; reached two Champions League finals; and claimed the Premier League Golden Boot (2010-11) in just four seasons, scoring 56 goals in 149 games. Plus he registered one of the greatest assists the league has ever seen.

8. James Milner, Man City to Liverpool, July 2015, Free

Milner was a teenage sensation at Leeds who was already the embodiment of professionalism and consistency when he signed for Man City for £26m in 2010. He joined Liverpool on a free transfer, and the utility player formed part of Brendan Rodgers’ rebuild at Anfield after the exit of long-serving club legend Steven Gerrard. Seven years later, Milner remains a popular figure at Liverpool under Klopp, while he continues to defy his advancing age (he’ll turn 37 this season). The veteran has already made more than 800 club appearances in his long career and shows no real signs of slowing up. By winning the Premier League, FA Cup, League Cup, Champions League, UEFA Super Cup and the Club World Cup, Milner has also won more trophies in his seven seasons at Liverpool than at all of the other clubs he has represented combined.

7. Michael Carrick, Tottenham to Man United, July 2006, £24.4m

Already an established England international, Carrick became Man United’s sixth-most-expensive signing of all time and was ever present from his debut season onwards. He played an understated but important role in many of the club’s great triumphs in the decade that followed, including five Premier League titles, the 2007-08 Champions League and the Europa League trophy in 2016-17. In 12 years as a player at Old Trafford, Carrick managed to win every domestic honour in English football. He is also the only English player aside from former United teammate Wayne Rooney to win the Premier League, FA Cup, Champions League, League Cup, FA Charity/Community Shield, Europa League and the Club World Cup. After retiring at the end of the 2017-18 campaign, Carrick joined the first-team coaching staff at United and even served as caretaker manager for a three-match stint in November 2021 following the dismissal of Ole Gunnar Solskjaer.

6. Robin van Persie, Arsenal to Man United, August 2012, £27.6m

Van Persie had largely shaken off his notorious injury problems and had fully established himself as a top striker by 2011-12, when he scored 44 goals in 57 games for club and country. Manchester United, meanwhile, had just suffered the heartache of losing a watershed title race to Manchester City on goal difference. So it was no surprise that United manager Sir Alex Ferguson singled out Van Persie as the missing piece needed to help reclaim superiority. Unsurprisingly, Arsene Wenger and Arsenal didn’t feel quite as enthused about the prospect of losing their club captain and top scorer — who had only one year remaining on his deal — to a rival club. After a series of low-ball offers and snubbed contract extensions, United finally managed to get their deal over the line in mid-August. After the deal was completed, Ferguson admitted that he never truly believed he would be able to prise the Gunners’ star striker away. Van Persie finished as United’s top scorer, with 30 goals in 48 games, and retained the Premier League Golden Boot the 2012-13 as Ferguson oversaw a 13th Premier League title win in what would be his final season in charge before retirement. With United in flux, the Dutch striker spent two further seasons at Old Trafford but was unable to replicate the majesty of his debut year. Injuries, coupled with the team’s general malaise, saw his numbers fall away, and he left for Fenerbahce in 2015. No matter, his transfer had served its purpose, restoring United to the top of English football and weakening a direct rival.

5. Sol Campbell, Tottenham to Arsenal, July 2001, Free

Campbell’s name is still hissed with malice among aggrieved Tottenham fans due to the manner in which the centre-back engineered his free transfer across North London. With his contract set to expire that summer, Spurs offered the defender fresh terms that would have seen him become one of the club’s top earners. Negotiations dragged on, several public assurances that he was intending to stay at Spurs were made from Campbell, then out of the blue, he was formally unveiled as an Arsenal player without anybody — not even the national press — any the wiser. As the first player to move between Arsenal and Tottenham in the Premier League era, Campbell’s shocking defection earned him the derogatory Biblical nickname “Judas” within Tottenham circles. However, he proved to be a transformative signing for the Gunners, winning two Premier League titles (one as an “Invincible” in 2003-04) and three FA Cups and even scoring in a Champions League final during the club’s golden run of success under Wenger, before leaving for Portsmouth in 2006.

4. Kyle Walker, Tottenham to Man City, July 2017, £47.4m

After beginning his career at boyhood club Sheffield United and then furthering it at Tottenham, Walker made the leap to Man City in the summer of 2017 in an enormous transfer that could have feasibly made him the most expensive English player ever once all add-ons and clauses were activated. The versatile England international defender has been a near-constant presence for City ever since, playing 214 times at right-back, wing-back, centre-back, defensive midfield, right midfield and even goalkeeper (in an emergency 10-minute cameo in the Champions League in 2019 against Atalanta, where he kept a clean sheet). Walker has won four Premier League titles at the Etihad, as well as four League Cups and one FA Cup, while continuing to be one of Pep Guardiola’s most trusted defensive options.

3. Teddy Sheringham, Tottenham to Man United, July 1997, £4.7m

Sheringham joined Spurs from Nottingham Forest in 1993 and finished as their top scorer in the Premier League in his debut season. The deep-lying striker quickly became a fan favourite at White Hart Lane and formed a strong partnership with German striker Jurgen Klinsmann. After finishing as top scorer again in 1996-97 as his side washed up in midtable and now 31 years old, Sheringham felt the time was right to move on in search of the first major club honour of his career. Manchester United, in need of a replacement for Eric Cantona following his shocking early retirement from professional football at age 30, was the obvious destination.

The England international hit the ground running at Old Trafford and scored 14 goals in 42 games in his first season, although that campaign ended in Arsenal winning the double. Gunners fans revelled in reminding the former Spurs star of that fact over the course of the 1998-99 season, but he had the last laugh when he helped United go one better by the end of the campaign. Indeed, it was his precious goal and assist deep into injury time that would see United pull off a momentous comeback win over Bayern Munich to win the 1999 Champions League final, thus completing their unprecedented Treble.

Sheringham spent four seasons with United and won three Premier League titles, one FA Cup, the Champions League and the Intercontinental Cup. His final season (2000-01) saw the veteran recapturing his finest form at age 35, with his 21 goals in 43 games and winning him both the PFA Players’ Player of the Year and FWA Footballer of the Year awards before he returned to Spurs.

2. Ashley Cole, Arsenal to Chelsea, August 2006, £6.6m

One of the most controversial transfers of the Premier League era saw Cole leave Arsenal under a cloud that was largely of his own making. Already regarded as a world-class left-back, Cole won two Premier League titles and three FA Cups with the Gunners and as part of the 2003-04 “Invincibles.” The problems began when Cole was found to have breached rules by going behind Arsenal’s back to meet with a Chelsea contingent to discuss a potential move. The defender was fined by both the Premier League and Arsenal, but eventually agreed a one-year contract extension.

The uneasy truce didn’t last: Cole used his autobiography, “My Defence,” to lambast Arsenal for supposedly making him a scapegoat over the Chelsea scandal as well as reveal that he “nearly swerved off the road” and was left “trembling with anger” by what he deemed a derisory offer of a pay rise. It was at this point the “Ca$hley” nickname was born.

Transfer negotiations with Chelsea (permitted, this time) rumbled on for several months before a £6.6m transfer was agreed, with centre-back William Gallas moving the other way. Cole spent eight highly successful seasons at Stamford Bridge, playing 336 times while winning the Premier League, four FA Cups (seven overall, the most ever by a single player), one League Cup, the Champions League and the Europa League.

1. Raheem Sterling, Liverpool to Man City, July 2015, £49m

Man City making a winger barely out of his teens the most expensive English player ever was questioned by many at the time, but the signing was quickly vindicated as Sterling became one of the pivotal players in the club’s transition from nouveau riche upstarts to bona fide Premier League behemoths.

They said he couldn’t shoot, and yet no player scored more goals for City in the Guardiola era than Sterling (120 in all competitions since the start of the 2016-17 season), with the forward registering 131 goals and 94 assists in 337 competitive games. Despite rarely playing as a central striker, Sterling achieved a milestone 30-goal season in 2019-20 (31 goals in 52 games) as he hit peak form for club and country, adding a further nine goals in 11 games for England to his career-high total over those two years. For a period he seemed truly unstoppable.

A vital cog in the Guardiola machine, Sterling won four Premier League titles, an FA Cup and five League Cups with City. He was also part of the side that broke new ground by reaching the club’s first-ever Champions League final, only to lose to Chelsea in the 2020-21. A year later, Sterling joined the Blues for roughly the same fee that City paid for him seven years previously, which was a great deal for all concerned.





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