Ruud Gullit (P4, W4, D0, L0)
Player-manager Gullit took the reins at Chelsea in May 1996, four months before Wenger arrived at Arsenal, and the pair were the only non-British or Irish managers in the Premier League in the 1996/97 campaign. Wenger’s late appointment meant he missed the season’s first clash between the two clubs in early September – a thrilling 3-3 draw – while the reverse fixture ended in a comfortable 3-0 Arsenal win in April. Wenger celebrated three more victories over Gullit the following season, twice in the league and once in the Coca-Cola Cup semi-final, before the Dutchman was dismissed in February 1998 to take his not-so-sexy football to Newcastle.
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Gianluca Vialli (P7, W3, D2, L2)
The 33-year-old Vialli was selected as Gullit’s replacement, with the second leg of that cup tie his first match in charge. The Italian got off to a flying start as Chelsea overturned a one-goal deficit to win 4-3 on aggregate and book their place in the final, where they defeated Middlesbrough 2-0.
Vialli recorded a stunning 5-0 triumph over Arsenal at Highbury in the same competition in 1998/99, although Wenger came out on top in the league: the first game between the sides ended 0-0, but Arsenal ran out narrow 1-0 winners in January. The north Londoners then did the double over Chelsea the following season, before back-to-back draws with Arsenal and Newcastle in September 2000 meant Vialli was sacked.
Claudio Ranieri (P14, W8, D5, L1)
Although Arsenal and Chelsea were both fighting for major honours during the early 2000s, Wenger enjoyed an amicable relationship with Ranieri. Perhaps the most memorable meeting between the two men was the only occasion on which the Italian triumphed, Wayne Bridge’s late strike in the second leg giving Chelsea a 3-2 aggregate victory in the Champions League quarter-final in 2004. Wenger completely dominated other than that, with a 2-0 win in the 2002 FA Cup Final securing his and Arsenal’s second domestic double in five years.
Jose Mourinho (P14, W0, D6, L8)
There have been few managerial feuds laced with as much rancour as Mourinho and Wenger’s; whereas the Frenchman’s rivalry with Sir Alex Ferguson was driven more by competition than personality, there was often an element of downright nastiness to his battles with the self-proclaimed Special One.
In truth, Mourinho – who saw Wenger’s idealism as the antithesis to his hard-nosed pragmatism – was usually the aggressor, with his labelling of the Arsenal boss as a "voyeur" in 2005 and "specialist in failure" in 2014 considered by many to be two steps too far. On the pitch, though, it was the Chelsea man who continually enjoyed the upper hand: Mourinho won eight of 14 competitive games with Wenger, with the other six ending in draws. A 6-0 thrashing at Stamford Bridge in Wenger’s 1,000th match as Arsenal boss will go down as one of the lowest points in his managerial career.
Avram Grant (P2, W1, D0, L1)
Grant’s stay at Chelsea was short and so very nearly sweet, with the Blues narrowly missing out on their maiden Champions League crown after losing a penalty shoot-out to Manchester United in May 2008. Unsurprisingly given Grant’s calmer, less confrontational style in relation to predecessor Mourinho, Chelsea’s encounters with Arsenal were rather low-key in 2007/08: both teams won their Premier League home match against the other as the duo finished just a few points behind champions United.
Luiz Felipe Scolari (P1, W1, D0, L0)
“I have known him a long time… I met him in Japan because he was over there, although he didn't stay for very long because he didn't like the sushi,” Wenger told Arsenal’s official website ahead of his team’s trip to Chelsea in November 2008. “I believe he has done well. He is a very experienced, extroverted man who does well.”
That game, which Arsenal won 2-1 thanks to a brace from Robin van Persie, was the only one Wenger and Scolari contested in England before the latter’s sacking in February – a decision that Wenger called a “massive surprise”.
Guus Hiddink (P3, W0, D0, L3)
Hiddink extended his 100% winning record in England against the Frenchman with 2015/16's 1-0 win over the Gunners at the Emirates Stadium, in which Per Mertesacker was sent off after 18 minutes and Diego Costa secured the win five minutes later. In Hiddink's first spell as Blues caretaker, Chelsea thrashed Arsenal 4-1 in May 2009 to wrap up third place in the top flight, and also reached the FA Cup final – which they won – at the north Londoners' expense with a 2-1 semi-final success.
Carlo Ancelotti (P4, W1, D0, L3)
Real Madrid received a fair amount of flak for dispensing of Ancelotti after one trophyless season, but Florentino Perez wasn't the first boardroom heavyweight to prematurely send the Italian packing: when Roman Abramovich terminated his contract in 2011, the consensus was that he had made a major mistake.
Wenger only won one of four meetings with Ancelotti’s Chelsea, a 3-1 league victory in December 2010. While the pair’s relationship was generally friendly, there were a few occasions where thinly veiled insults were thrown from both sides. When Wenger mischievously suggested that Chelsea would continue to drop points after a patchy run of form in the former Milan boss’s first campaign at the helm, for example, Ancelotti branded him a “good magician”.
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Andre Villas-Boas (P1, W1, D0, L0)
Wenger and Villas-Boas’s sole duel featured eight goals as Arsenal capitalised on Chelsea’s lethal combination of slow centre-halves and a high defensive line to win 5-3 at Stamford Bridge. Wenger was again implicitly critical of Abramovich when the then-35-year-old was dismissed in March 2012, admitting he “felt sorry for Villas-Boas because I like him as a manager and as a man”.
Roberto Di Matteo (P2, W0, D1, L1)
Despite only being in charge for six months, Di Matteo will go down as one of the most popular Chelsea managers in history after he won an unlikely Champions League title in May 2012. He also possessed a decent record against Wenger and Arsenal, which is always bound to help a Chelsea coach’s image.
A 0-0 draw away from home extended the Blues’ unbeaten run in all competitions to nine games towards the end of the 2011/12 campaign, while a 2-1 triumph in September of the subsequent season cemented the west Londoners’ position at the top of the table.
- Roberto Di Matteo, One-on-One
Rafael Benitez (P1, W0, D0, L1)
It’s safe to say that Benitez was never a fans’ favourite during his short reign at Stamford Bridge. He did, however, receive support and backing from Wenger, who insisted history would judge his spell as interim boss favourably. The managers’ only encounter ended in a 2-1 Chelsea win, with early goals from Frank Lampard and Juan Mata enough for Benitez’s charges to secure a vital victory at the turn of the year in 2013.
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There is no greater evidence of the juxtaposition between Wenger’s longevity and Chelsea’s trigger-happy culture than the fact that, Mourinho aside, the Arsenal manager has averaged just 2.4 matches against each Chelsea coach since Ranieri.
Antonio Conte (P5, W2, D2, L1)
There was a rude awakening for new Chelsea boss Conte in September 2016 – a 3-0 thumping at the Emirates Stadium in which Arsenal had scored all their goals by half-time. It was the Blues' second defeat in their first six games of the season, but it proved a turning point – they won their next 13 consecutive Premier League games, equalling Arsenal's record from their own 2001/02 title-winning campaign, and romped to the league title. Wenger was triumphant in the 2017 FA Cup Final, however, and then again in the Community Shield that followed. Most recently, the two bosses' teams duked out a goalless draw.
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