Which moment will Arsene Wenger look back on from his 22 years at Arsenal with the most disdain? Here is a selection of occasions Wenger would rather forget, and we ask you to vote for the worst…
Tottenham 5-1 Arsenal – 22nd January 2008
With Wenger having a penchant for fielding a second string in the League Cup, Tottenham would have been confident of sneaking victory at home in the Carling Cup final second leg, having drawn at the Emirates in the first leg, but even Spurs fans could not have imagined in their wildest dreams that they would earn a first win over their north London rivals in nine years in such a comprehensive manner. Goals from Jermaine Jenas, a Nicklas Bendtner own goal, Robbie Keane, Aaron Lennon and Steed Malbranque did the damage, with Bendtner and Emmanuel Adebayor having to be separated near the end of the match.
Birmingham 2-2 Arsenal – 23rd February 2008
Leading the Premier League by five points coming into a trip to St Andrew’s to take on relegation-threatened Birmingham, Arsenal looked on course to wrestle the title back from Manchester United, but a damaging draw in the Midlands ultimately led to Arsenal crumbling under the pressure. It was difficult to focus on the football after Eduardo’s horrific early injury that saw Martin Taylor given his marching orders, but Arsenal battled back from a goal down to lead 2-1 against the 10 men coming into stoppage time, only to see a late penalty cost them two crucial points. Captain Gallas was inconsolable at the final whistle, punching the ground in hysterics, leading many to question Arsenal’s mental fragility. Such doubts proved warranted as Arsenal won just one of their next seven league games as United retained their title.
Birmingham 2-1 Arsenal – 27th February 2011
Attempting to end a six-year trophy drought, Birmingham represented the perfect opponent in the League Cup final at Wembley, and with the big guns restored to the starting XI for the showpiece Arsenal were red-hot favourites. Nikola Zigic did give Birmingham the lead, only to see his strike cancelled out by Robin van Persie. The Gunners pressed and pressed, but astonishingly, in calamitous style, Obafemi Martins netted a last-gasp winner for Birmingham, after Laurent Koscielny and Wojciech Szczesny made an absolute mess of a routine long ball.
Wenger described his relationship with Arsenal football club as a "love story"
Manchester United 8-2 Arsenal – 28th August 2011
Everything that could have gone wrong for Wenger did as United dismantled Arsenal at Old Trafford, 10 years on from another Dwight Yorke-inspired thrashing. Arsenal were hit by injuries, but they were up against a United side many felt lacked their former grandeur. Nevertheless, a makeshift back four of Carl Jenkinson, Johan Djourou, Koscielny and Armand Traore – who never played for Arsenal again after this encounter – were at sixes and sevens all afternoon. It was too easy for the champions United, who romped to an 8-2 victory, with Wayne Rooney helping himself to a hat-trick. The image of Wenger, arms outstretched after being sent to the stands by the referee, unsure of where to stand, is one of the most enduring images in Premier League history.
Chelsea 6-0 Arsenal – 22nd March 2014
Anniversary occasions are meant to be cause for celebration, where you take a nostalgic journey back through your finest moments over a certain period, but Wenger’s 1,000th game in charge of Arsenal will be one he instantly wanted to forget. Arsenal were two behind after seven minutes, with first Samuel Eto’o and then Andre Schurrle benefiting from clinical Chelsea counter-attacking, before Kieran Gibbs was sent off for handball, when it was in fact Alex Oxlade-Chamberlain who had committed the infringement. The goals continued to rain in on the Arsenal goal, with the final score the joint-heaviest margin of defeat suffered by Wenger at Arsenal, alongside the 8-2 defeat by United.
10-2 aggregate defeat to Bayern Munich in 2017
Wenger received a guard of honour from both sets of players ahead of his final game at the Emirates Stadium.
At the height of the “Wenger Out” pandemic at the Emirates, Bayern Munich were in town, and made matters a whole lot worse. Wenger’s latter-years at Arsenal have suffered some grim European capitulations, from what seemed like the annual defeat to Barcelona, to the 2015 loss to Monaco – they have all been dispiriting in their own way. But the 10-2 aggregate humiliation by Bayern last season surely topped them all. Being beaten by Bayern is not necessarily embarrassing, but the manner of their capitulation was. At the end of the second leg, at the Emirates, on the back of a second successive 5-1 defeat, the home fans were not even sure how to channel their anger.
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