Petr Cech is edging closer to a switch from Chelsea to Arsenal but seeing as he has not yet represented the Gunners, he cannot be placed on this list. Rest assured, had he played for the two sides, the towering Czech would have been one of the names. Of the five names that follow, all have played for Arsene Wenger whereas current Chelsea manager Jose Mourinho has only managed three out of the five in his two spells at Chelsea.

Ashley Cole:

Arguably the best left-back of his generation and a player generally considered to be the best left back in Premier League history, the now-Roma man made the direct switch from Arsenal to Chelsea in 2006. His transfer between the two sides was surrounded in controversy; in the summer of 2005, first contact between Mourinho and Cole was made but nothing came of it.

A year later and Cole had been offered a new contract at Arsenal of £55,000 a week which left him “trembling with anger” whereas Chelsea offered £90,000 a week. On the final day of the 2006 summer transfer window, the deal was done with Chelsea paying £5 million and William Gallas going the other direction as part of the deal. At Chelsea, Cole would end up winning every available trophy in domestic and European club football. Four FA Cups, a Premier League, a League Cup, one Europa League, one Community Shield and one Champions League later and Cole is now labelled by Chelsea fans as a legend. Arsenal fans tend to label Cole with less affectionate terms, sometimes "Cashley", sometimes something a bit more crude.

Cole's time at Arsenal was also full of trophies. Part of the famous 'Invincible' side of 2003-2004, Cole also won the 2001-2002 Premier League as well as three FA Cups and two Community Shields, making a total of 228 appearances for the Gunners in all competitions. At Chelsea, Ashley Cole made 110 more appearances in all competitions than at Arsenal, the England centurion wrapping up his Chelsea career with 338.

Cesc Fabregas:

Going from Arsenal to Chelsea via a three year stop-off at Barcelona, the club Arsenal originally pinched him from as a youth player following an impressive U-17 World Cup campaign with Spain in 2003, Fabregas is currently playing for the Blues as of the 2014 summer transfer window. Arsenal acquired Fabregas from Barcelona as a 16-year-old and the Spanish star would establish himself as one of the world’s top playmakers in his eight year spell with the North London side.

Ultimately, Fabregas outgrew the club’s ambitions and left the Gunners, a team he was club captain of, for childhood side Barcelona as Arsenal were in a transition phase and had to sell their top players to pay off the cost of their move from Highbury to the Emirates. He played 303 times for Arsenal in all and scored 57 goals, only winning the FA Cup in 2005 and the Community Shield in 2004.

Six trophies in three seasons at Barcelona later and Fabregas had become unhappy at the Catalan club as a result of being played out of position and not being played as consistently as he would have liked. Chelsea signed him for £27 million and Fabregas would end up winning a double of the Premier League and League Cup in his first season with Chelsea, being a main cog in the Mourinho machine, playing as a deep lying playmaker next to the more defensive Nemanja Matic in a 4-2-3-1.

Emmanuel Petit:

Just like Cesc Fabregas, Petit made the move from Arsenal to Chelsea via a stop-off at Barcelona. Petit played for Arsenal for three years, from 1997 to 2000, forming a formidable defensive midfield partnership with Patrick Vieira. It was Wenger who converted him from central midfield to a more defensive role and it was with Wenger’s side that the Frenchman would enjoy his most successful years, winning a Premier League, FA Cup and two Charity Shields, along with the 1998 World Cup with France.

After one year with Barcelona, who bought Petit for £7 million, Petit returned to England by going to Chelsea, and would also end up spending three seasons with the Blues. His first season for the Blues was rather disappointing, with the only thing of note being a FA Cup final defeat at the hands of old team Arsenal by a score of two goals to nil. The second season with Chelsea would be significantly better, as Petit formed a midfield partnership with the young Frank Lampard, a player Chelsea had recently bought for £11 million from London rivals, West Ham.

Chelsea clinched Champions League qualification in a decisive match against Liverpool which allegedly caused Russian billionaire Roman Abramovich to choose Chelsea over Liverpool as the team he would buy. Petit’s final season with Chelsea resulted in only seven appearances in all competitions as his season was ruined by a series of knee injuries. The injuries would be so severe that Petit would then retire a season later after failing to recover fully.

Nicolas Anelka:

The French striker is the epitome of the word ‘journeyman’, having played for 12 separate teams and six in England alone. Wenger signed Anelka from Paris Saint-Germain when Anelka was only 17-years-old and had just completed his first professional season. The fee was half a million and the transfer was completed in February of 1997 but Anelka’s first team opportunities were limited that season. The following season, Anelka broke into the team following an injury to Ian Wright and was a key player in the Arsenal team that won the domestic double.

1998-1999 was also another successful season for Anelka with the Gunners. 17 goals in the Premier League saw him voted the PFA Young Player of the Year but his perceived lack of enthusiasm, giving him the nickname “Le Sulk”, and ongoing transfer speculation saw him transfer to Real Madrid in the summer of 1999 for just over £22 million.

His four year spell at Chelsea would be marginally more successful as Anelka ended up winning one Premier League, two FA Cups and a Community Shield. The 2008-2009 season was successful for Anelka personally as the Frenchman won the Premier League Golden Boot but it was as part of a trifecta of Malouda, Drogba and Anelka that saw Anelka gain the most team success.

The 2009-2010 season was a double winning campaign for Chelsea and the attacking trio, well supported by Frank Lampard, ended up allowing Chelsea to score the most goals in one season in Premier League history: 103. Anelka ended up departing the club in the January transfer window of 2011-2012 in acrimonious circumstances, having been frozen out the side by Andre Villas Boas and forced to train with the youth players.

William Gallas:

The French defender was bought to Chelsea by Claudio Ranieri in 2001 for a fee of £6.2 million. Given the number 13 shirt, Gallas formed a partnership with fellow Frenchman Marcel Desailly and then with Chelsea Academy graduate and future club captain, John Terry. At Chelsea, Gallas was part of the side that won back-to-back Premier League titles in 2005 and 2006 as well as a League Cup and Community Shield. His last season at Chelsea saw him played at left back due to an injury to Wayne Bridge but the versatility Gallas possessed saw him have no troubles adapting. He transferred to Arsenal as part of the deal that saw Ashley Cole go the other way.

Given the number 10 shirt by Wenger, the number worn by the then just-retired Arsenal legend, Dennis Bergkamp, Gallas’ time at Arsenal was forgettable for a multitude of reasons. Firstly, he did not win anything with Arsenal. Secondly, Gallas was stripped of the captaincy he had earned in his second season with the club midway through his third season with the Gunners following comments made about tension within the squad and stating that the young players would have to show more courage. The captaincy was given to Cesc Fabregas. Thirdly, Gallas joined North London rivals, Tottenham Hotspur after rejecting a contract offer from Arsenal.

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About the author
Indrit Berisha
Love football, love Chelsea. Will talk about anything, from any player to any team. Enjoy playing the sport, enjoy watching it, enjoy writing about it.