1. Round | 16/08/2008 | Middlesbrough FC | - | Tottenham Hotspur | 2:1 | ||||
2. Round | 23/08/2008 | Tottenham Hotspur | - | Sunderland AFC | 1:2 | ||||
3. Round | 31/08/2008 | Chelsea FC | - | Tottenham Hotspur | 1:1 | ||||
4. Round | 15/09/2008 | Tottenham Hotspur | - | Aston Villa | 1:2 | ||||
6. Round | 28/09/2008 | Portsmouth FC | - | Tottenham Hotspur | 2:0 | ||||
7. Round | 05/10/2008 | Tottenham Hotspur | - | Hull City | 0:1 |