| League | Date | Home Team | Score | Away Team |
|---|---|---|---|---|
| PL | 24-05-2009 | Liverpool | 3 - 1 | Tottenham |
| PL | 16-05-2009 | Tottenham | 2 - 1 | Man City |
| PL | 09-05-2009 | Everton | 0 - 0 | Tottenham |
| PL | 02-05-2009 | Tottenham | 1 - 0 | West Brom |
| PL | 25-04-2009 | Man United | 5 - 2 | Tottenham |
| PL | 19-04-2009 | Tottenham | 1 - 0 | Newcastle |
| PL | 11-04-2009 | Tottenham | 1 - 0 | West Ham |
| PL | 04-04-2009 | Blackburn | 2 - 1 | Tottenham |
| PL | 21-03-2009 | Tottenham | 1 - 0 | Chelsea |
| PL | 15-03-2009 | Aston Villa | 1 - 2 | Tottenham |
| PL | 07-03-2009 | Sunderland | 1 - 1 | Tottenham |
| PL | 04-03-2009 | Tottenham | 4 - 0 | Middlesbrough |
| PL | 23-02-2009 | Hull | 1 - 2 | Tottenham |
| PL | 08-02-2009 | Tottenham | 0 - 0 | Arsenal |
| PL | 31-01-2009 | Bolton | 3 - 2 | Tottenham |
| PL | 27-01-2009 | Tottenham | 3 - 1 | Stoke |
| PL | 18-01-2009 | Tottenham | 1 - 1 | Portsmouth |
| PL | 11-01-2009 | Wigan | 1 - 0 | Tottenham |
| PL | 28-12-2008 | West Brom | 2 - 0 | Tottenham |
| PL | 26-12-2008 | Tottenham | 0 - 0 | Fulham |
| PL | 21-12-2008 | Newcastle | 2 - 1 | Tottenham |
| PL | 13-12-2008 | Tottenham | 0 - 0 | Man United |
| PL | 08-12-2008 | West Ham | 0 - 2 | Tottenham |
| PL | 30-11-2008 | Tottenham | 0 - 1 | Everton |
| PL | 23-11-2008 | Tottenham | 1 - 0 | Blackburn |
| PL | 15-11-2008 | Fulham | 2 - 1 | Tottenham |
| PL | 09-11-2008 | Man City | 1 - 2 | Tottenham |
| PL | 01-11-2008 | Tottenham | 2 - 1 | Liverpool |
| PL | 29-10-2008 | Arsenal | 4 - 4 | Tottenham |
| PL | 26-10-2008 | Tottenham | 2 - 0 | Bolton |
| PL | 19-10-2008 | Stoke | 2 - 1 | Tottenham |
| PL | 05-10-2008 | Tottenham | 0 - 1 | Hull |
| PL | 28-09-2008 | Portsmouth | 2 - 0 | Tottenham |
| PL | 21-09-2008 | Tottenham | 0 - 0 | Wigan |
| PL | 15-09-2008 | Tottenham | 1 - 2 | Aston Villa |
| PL | 31-08-2008 | Chelsea | 1 - 1 | Tottenham |
| PL | 23-08-2008 | Tottenham | 1 - 2 | Sunderland |
| PL | 16-08-2008 | Middlesbrough | 2 - 1 | Tottenham |