2. The Birmingham Catastrophe
Simon Dawson/AP/Press Association ImagesArsenal's 8-2 hiding against Manchester United was a game to forget. Their 2-1 defeat to Birmingham was worse. It was February 2011, and the Gunners had entered a sixth season without winning a trophy. However, they were presented with a golden opportunity to end the drought when they faced Premier League strugglers Birmingham City in the League Cup final. Birmingham would go on to finish 18th and be relegated into the Championship three months after this game, yet Alex McLeish's side sprung the most almighty surprise here at Wembley. Arsenal experienced their first moment of panic on the half-hour mark when Nikola Žigi opened the scoring for City, though Robin van Persie restored parity 11 minutes later. Despite this, the Gunners failed to make their dominance count. Samir Nasri, Andrei Arshavin and Nicklas Bendtner were all denied by Ben Foster, and their profligacy in front of goal was punished on the 89 minute mark when Obafemi Martins capitalised on a misunderstanding between Gunners goalkeeper Wojciech Szczesny and defender Laurent Koscielny to strike the late blow that extended Arsenal's wait for a trophy into another year. This was a game Arsenal really should have won, and it was the best chance Wenger ever had of ending the crippling trophy drought that until this year hung over the club like a thundercloud. Yet he was unable to mastermind a way past the Premier League's basement boys, and wrote another ignominious chapter into Arsenal's history books.