12 Chelsea managers Arsene Wenger has faced in the last 21 years - #4 and #7 are his greatest enemies | Page 12 of 12

Arsene Wenger has faced 12 Chelsea managers in 58 clashes over the years: how has the Arsenal boss fared vs Jose Mourinho, Claudio Ranieri and Co? Arsene Wenger today signed another contract extension to stay as Arsenal manager for the next 2 years. Over the course of 1,177 matches, he has revolutionised the English game and provided more than his fair share of drama. Over the duration of his time at Highbury and the Emirates, Wenger has come up against Chelsea 54 times, be it in the Premier League, domestic cups or on the European stage. More..

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1. Ruud Gullit (1996-1998)

When Wenger was unveiled as the new Arsenal boss in September 1996, the general consensus was one of confusion. Down the road in west London, another new manager - a more household name - was beginning his time in charge of Chelsea. Wenger was too late to take charge of Arsenal vs Chelsea that season - a brilliant 3-3 draw at Highbury in which Dennis Wise scored a 90th minute equaliser - but he did take charge of the reverse fixture in April. Wenger led his side to a 3-0 away rout at the Bridge, and in fact held a perfect record over his rival. Gullit left Chelsea in 1998 having played four games against Arsenal... and he lost them all.

2. Gianluca Vialli (1998-2000)

At 33 years old, Gianluca Vialli was still playing when he took over the managerial reigns at Chelsea, and in his two years at the helm he faced Wenger seven times. In fact, Wenger had much to do with the arrival of the Italian to the dugout. On October 8, his side beat Chelsea 2-0, and Gullit was sacked four days later. Up stepped Vialli, with a League Cup semi-final clash against Arsenal to look forward to just six days into his reign. You could have forgiven Wenger for expecting a victory. A league win just days previous, Chelsea in disarray... well, that certainly wasn't the case. Patrick Vieira was sent off just after half-time, and the Blues stuck three past Alex Manninger to secure a victory.

3. Claudio Ranieri (2000-2004)

Wenger has only faced Jose Mourinho more times than Claudio Ranieri in his clashes with Chelsea over the years. The now-Leicester manager came up against the Arsenal boss 14 times in his four seasons at the Bridge. Their first league clash - in January 2001 - saw the two sides share the spoils as a 20-year-old John Terry netted a second-half equaliser. They faced each other once more that season, in the fifth round of the FA Cup, and Arsenal ran out 3-1 winners on their way to the semi-final of the competition. Wenger got the better of Ranieri on many an occasion, only losing once in their 14 clashes. That said, he would no doubt swap all of that for another little taste of the title, just as the Tinkerman did with Leicester last season.

4. Jose Mourinho (2004-2007; 2013-2015 ) In 15 clashes with Mourinho, Wenger won just one. A rivalry that has spanned decades, a war of words that still drags on to this day with Mourinho in charge of Manchester United. Just this week, Sportsmail revealed new quotes from Mourinho in which he claimed: 'I will find him one day outside a football pitch and I will break his face.' That said, our focus is inside the football pitch, and on Wenger's incredible 6.7 per cent win record over Mourinho at Chelsea. The first time they locked horns was in Chelsea's title-winning season, when Arsenal finished runners-up but still managed to lift the FA Cup.

They drew twice that season, but things took a turn for the worse in 2005-06 when Chelsea beat Arsenal in the Community Shield (a 2-1 win with Didier Drogba scoring both), before going on to two impressive Premier League triumphs. That season, Chelsea won the title again, Arsenal scraped to fourth, and the rivalry intensified. Mourinho left Chelsea in 2007 for pastures new, but returned in 2013 to reignite the fire. You will remember the famous handbags moment on the touchline as the pair pushed and shoved each other. That was October 2014, a 2-0 win for Chelsea. There was also an incredible 6-0 Chelsea win in March of the same year, yet another Mourinho victory over his old foe. In fact, the only time Wenger got one over on Mourinho the Chelsea manager was last year, the 2015 Community Shield. The Frenchman swerved his old enemy's handshake, before Alex Oxlade-Chamberlain secured a sweet, sweet victory.

5. Avram Grant (2007-2008) A fairly simple rivalry ensued between Wenger and Avram Grant. The Israeli was at Stamford Bridge for one season... Arsenal and Chelsea played twice in the league, with a home win for each side. Two goals for, two goals against. That term, Chelsea finished second and Arsenal were lagging just behind in third.

6. Luiz Felipe Scolari (2008-2009) There was an even less fiery relationship between Wenger and Luiz Felipe Scolari, as the Brazilian didn't even last a season at the Bridge. Their one clash came in west London, as Robin van Persie netted a three-minute double to secure three points for Wenger and push Scolari nearer to the exit door. The two sides did play twice further that season, but it was Guus Hiddink at the helm...

7. Guus Hiddink (2009; 2015-2016) Guus Hiddink had two spells at Chelsea, but wasn't at the Bridge long enough to forge anything like a serious rivalry with an opposition manager. That said, Wenger doesn't have happy memories of facing the now 69-year-old. In his first spell after taking over from Scolari, Hiddink was only at the club for three months, but he managed to squeeze in two victories over Arsenal. The first was the FA Cup semi-final, as Florent Malouda and Drogba cancelled out Theo Walcott's opener, and then Hiddink compounded the misery with a stunning 4-1 league win at the Emirates. In his recent spell at the helm, following Mourinho's second exit, he secured a third win without reply against Wenger. Per Mertesacker's early red card set the tone for the day, and Diego Costa secured the three points just a few minutes later. Oops.

8. Carlo Ancelotti (2009-2011) Carlo Ancelotti is a very successful coach, with three Champions League titles to his name, and major trophies in four different countries around Europe. And Wenger will be well aware of that, having been on the losing side three of the four times they met in English football. In the 2009-10 season, Chelsea struck five past Arsenal without reply, and the following season started much the same as Drogba caused Wenger yet more misery in October. Wenger finished with a flourish though, securing a much-needed win before Ancelotti left his position. It was the Emirates in 2010, just two days after Christmas, when Arsenal received a late gift courtesy of Alex Song, Cesc Fabregas and Walcott. Branislav Ivanovic pulled one back, but the points stayed safely in north London.

9. Andre Villas-Boas (2011-2012)

Such is the nature of modern football and the short length of time afforded to Premier League managers, Andre Villas-Boas and Wenger only met once. That said, it was an eight-goal thriller with the Gunners running out 5-3 winners. It was 3-3 with just 10 to play, before Van Persie scored twice to complete his hat-trick and send the away fans home happy. Andre Santos and Walcott scored the other two goals.

10. Roberto Di Matteo (2012) Another short-term appointment that Arsene Wenger did not particularly enjoy. His Arsenal side faced Roberto Di Matteo's Chelsea twice in the space of eight months.

The games were split between seasons, with both matches coming at the Emirates and Arsenal winning neither. The first was a drab 0-0 draw, nothing like the mouthwatering eight-goal clash earlier that season.

At the start of the 2012-13 season, in which Arsenal eventually finished fourth, Chelsea travelled to the north of the capital and stole a much-needed three points. Gervinho pulled a goal back after Fernando Torres' opener, but Juan Mata was there to find a winner in the second half.

11. Rafael Benitez (2012-13) Another Chelsea manager, another 0 per cent win record for Mourinho. An unfortunate stat again, perhaps, as Wenger did only come up against Rafael Benitez once during the Spaniard's time at Stamford Bridge. The game was a Premier League affair, just after Christmas in January 2013. It was, impressively, Chelsea's fourth home game of the calendar year, and they'd not managed to pick up a win in any of their first three. Time for that to change though, as Juan Mata and Frank Lampard had the game tied up inside 16 minutes. Walcott - who has an impressive record against Chelsea over the years - pulled one back, but it wasn't enough to take a share of the spoils.

12. Antonio Conte (2016-2017) Arsene Wenger has played Chelsea's latest and current manager, Antonio Conte three times has won in two of the encounters, while Conte won one of the clashes: (Arsenal 3 - 0 Chelsea 24 Sep, 2016 - Premier League), (Chelsea 3 - 1 Arsenal 4 Feb, 2017 - Premier League) and (Arsenal 2 - 1 Chelsea 27 May - FA Cup Final) Arsene Wenger has declared his love for Arsenal after extending his contract for a further two years. The Frenchman, whose reign at the north London side already stands at more than two decades, has put pen to paper on fresh terms at the Emirates Stadium. Following months of unrest among groups of Gunners fans, with many becoming frustrated about a perceived lack of progress under Wenger, the 67-year-old's contract was ratified at a board meeting on Tuesday. This means Arsene Wenger has faced 11 Chelsea managers who have been sacked or resigned.

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