Arsene Wenger will face a familiar foe in an unfamiliar environment on Saturday when Arsenal travels to Manchester United.
The Arsenal boss will come up against bitter rival Jose Mourinho for the 15th time in his career, but it’s the first time he faces a different team than Chelsea under the Portuguese.
Wenger has never beaten Mourinho in a competitive game — with all due respect to the Community Shield — while he has lost eight of their 14 previous meetings.
Here is a look at five of the worst moments for the Frenchman against his old enemy …
Arsenal 0-2 Chelsea — Premier League, December 2005
The feud between the two managers had already begun after Chelsea dethroned Arsenal as Premier League champions the previous season, and Wenger had made his feelings clear about Mourinho’s style of play at the beginning of the campaign.
“I know we live in a world where we have only winners and losers, but once a sport encourages teams who refuse to take the initiative, the sport is in danger,” he said in a thinly veiled criticism of Mourinho’s defensive approach.
So it must have been all the more painful for Wenger when Chelsea came to Highbury and made sure Arsenal suffered a three-game losing streak in the league for the first time in more than a decade.
and Joe Cole scored to send Chelsea nine points clear at the top of the league, leaving Arsenal 20 points behind and completely out of the tiArjen Robbentle race.
Chelsea 2-1 Arsenal — 2007 League Cup final
The League Cup remains the one domestic competition Wenger has never won, in part because of Chelsea’s comeback in this testy match that laid bare the raw feelings between the two sides.
Didier Drogba established his reputation as Arsenal’s nemesis by netting both goals for Chelsea, and the game descended into a brawl at the end that saw three players sent off. A trophy here could have given an inexperienced Arsenal side the confidence boost they needed as Wenger tried to build around a team around young talents, but Mourinho made sure it was one of many setbacks Arsenal would suffer over the coming years.
Chelsea 6-0 Arsenal — Premier League, March 2014
Even before the match, Wenger probably would have wished to mark his 1,000th Arsenal game anywhere but at Stamford Bridge — but no one could have predicted how painful this one would turn out.
Arsenal were already behind 2-0 after seven minutes, and things only got worse when Andre Marriner mistakenly sent off Kieran Gibbs instead of Alex Oxlade-Chamberlain for handling on the goal line. Along with the 8-2 drubbing at Manchester United in 2011, this ranks among the worst defeats of Wenger’s career. And to prove just how painful it was, he didn’t even show up his for postmatch news conference.
Chelsea 2-0 Arsenal 0 — Premier League, October 2014
This defeat even saw the rivalry between the managers turn physical. Incensed by a tough tackle on Alexis Sanchez, Wenger strode into Chelsea’s technical area and pushed Mourinho hard in the chest when he tried to block the Frenchman’s path.
While the Arsenal fans loved the show of passion from Wenger, it didn’t help his team. Eden Hazard and Diego Costa scored to ensure another frustrating afternoon at Stamford Bridge for the Gunners.
Chelsea 2-0 Arsenal — Premier League, September 2015
Even in a season where Chelsea struggled so badly that Mourinho was sacked before Christmas, Wenger endured the same old story at Stamford Bridge. A disputed red card for Gabriel Paulista just before half time, when perhaps Costa should have been sent off instead, handed Chelsea the initiative, and they took full advantage after the break.
Wenger was left furious over the referee Mike Dean’s decision, and Chelsea’s and Mourinho’s continued struggles after this victory was probably of little consolation.