4. Tottenham 5-1 Arsenal, League Cup 2008
Look away Gooners, your side were completely destroyed in this outing at the Lane. And it was a vital game too, with this being the second leg of the League Cup semi-final.
This was Tottenham’s biggest win over their London rivals in 25 years and Wenger’s only second loss to them since he began to adventure at the Emirates in 1996.
Spurs were 2-0 up at half time, thanks to a goal from Jermaine Jenas and a Nicklas Bentdner own goal. Both Aaron Lennon and Robbie Keane quadrupled the Lilywhites’ lead before Emmanuel Adebayor pulled one back for Arsenal from somewhere.
Steed Malbranque scored the fifth, to round off a five-star performance against their old rivals.