2) 2011 – Birmingham City 2-1 Arsenal
Another game, another shock Arsenal defeat. Arsene Wenger’s side were in the midst of their lengthy trophy drought – ongoing since 2005 – and were desperate to lift a piece of silverware. In the most dramatic of circumstances, they were denied by Birmingham, who would go on to be relegated from the Premier League later that season. Robin van Persie had cancelled out Nikola Zigic’s opener, before Obafemi Martins capitalised on a defensive blunder from the Gunners to win it with almost the final kick of the match.