Watch: 5 worst defeats of Arsene Wenger's career

#2 February 27, 2011 – Birmingham City 2-1 Arsenal

Alex McLeish and his team knew the obvious that they were the underdogs in the final. Winning this match and subsequently ending the club’s 48-year long wait for a trophy was easier said than done. Arsenal, who were having a six-year trophy drought of their own saw this as the ideal opportunity to end it. However, things didn’t turn out to be the way the Gunners would have expected.

Arsenal, who were without Cesc Fabregas and Theo Walcott due to injury, found themselves trailing after 28 minutes as Nikola Zigic headed in Sebastian Larsson’s corner. Arsenal were nervous, complacent and shaky and on the other hand, Birmingham were playing with flair and confidence.

Robin van Persie equalised in the 39th minute but his failed side to score another as Ben Foster was in fine form and he pulled off some magnificent saves. Extra time looked a certainty before a horrendous mix-up between Laurent Koscielny and Wojciech Szczesny gifted Obafemi Martins a golden chance in the 89th minute.

Birmingham defeated Arsenal against all the odds and the day that was supposed to end in jubilation for Wenger and his team, ended in humiliation.