1. Round | 16/08/2008 | Middlesbrough FC | - | Tottenham Hotspur | 2:1 | ||||
4. Round | 15/09/2008 | Tottenham Hotspur | - | Aston Villa | 1:2 | ||||
6. Round | 28/09/2008 | Portsmouth FC | - | Tottenham Hotspur | 2:0 | ||||
8. Round | 19/10/2008 | Stoke City | - | Tottenham Hotspur | 2:1 | ||||
17. Round | 13/12/2008 | Tottenham Hotspur | - | Manchester United | 0:0 | ||||
18. Round | 21/12/2008 | Newcastle United | - | Tottenham Hotspur | 2:1 | ||||
19. Round | 26/12/2008 | Tottenham Hotspur | - | Fulham FC | 0:0 | ||||
20. Round | 28/12/2008 | West Bromwich Albion | - | Tottenham Hotspur | 2:0 | ||||
21. Round | 11/01/2009 | Wigan Athletic | - | Tottenham Hotspur | 1:0 | ||||
22. Round | 18/01/2009 | Tottenham Hotspur | - | Portsmouth FC | 1:1 | ||||
23. Round | 27/01/2009 | Tottenham Hotspur | - | Stoke City | 3:1 | ||||
24. Round | 31/01/2009 | Bolton Wanderers | - | Tottenham Hotspur | 3:2 | ||||
25. Round | 08/02/2009 | Tottenham Hotspur | - | Arsenal FC | 0:0 | ||||
26. Round | 23/02/2009 | Hull City | - | Tottenham Hotspur | 1:2 | ||||
28. Round | 04/03/2009 | Tottenham Hotspur | - | Middlesbrough FC | 4:0 | ||||
33. Round | 19/04/2009 | Tottenham Hotspur | - | Newcastle United | 1:0 |