| Tercera ronda | 24.09.2008 | Newcastle United | - | Tottenham Hotspur | 1:2 |  |
|||
| Octavos de final | 12.11.2008 | Tottenham Hotspur | - | Liverpool | 4:2 | |
 |
||
| Cuartos de final | 03.12.2008 | Watford FC | - | Tottenham Hotspur | 1:2 | |
|||
| Semifinales | 06.01.2009 | Tottenham Hotspur | - | Burnley FC | 4:1 | |
|||
| Semifinales | 21.01.2009 | Burnley FC | - | Tottenham Hotspur | 3:2 pró. | |
|||
| Final | 01.03.2009 | Manchester United | - | Tottenham Hotspur | 4:1 pn. |
Rusia