Watch: 5 worst defeats of Arsene Wenger's career

#3 January 22, 2008 – Tottenham Hotspur 5-1 Arsenal

Tottenham went into this game seeking the first win over their arch-rivals in nine years and a place in the Carling Cup final. The first leg finished 1-1 after Theo Walcott scored in the 79th minute to cancel out Jermaine Jenas’s opener.

The match had a start that Spurs fans would have dreamed of as Jermaine Jenas scored in the 4th minute. Things got even better for the hosts as Nicklas Bendtner scored an own goal that gifted Spurs a two goal cushion. Robbie Keane made it 3-0 shortly after the break and Aaron Lennon scored an emphatic fourth on the hour mark.

Emmanuel Adebayor pulled a goal back in the 70th minute but it was too little too late and Steed Malbranque’s 90th-minute goal completed Arsenal’s misery. The Gunners were frustrated to the core and a heated up argument between Bendtner and Adebayor during the match just summed it up.