| Matches by round |
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| Match list: | By round By date Latest | Player stats: | Cards All players |
| R | Date | Home | Score | Away | HT | >2.5 | HT | FT | |
| 1 | 8/10/2019 | Tottenham | 3 - 1 | Aston Villa | 0-1 | Yes | 2 | 1 | |
| 2 | 8/17/2019 | Manchester City | 2 - 2 | Tottenham | 2-1 | Yes | 1 | X | |
| 3 | 8/25/2019 | Tottenham | 0 - 1 | Newcastle | 0-1 | No | 2 | 2 | |
| 4 | 9/1/2019 | Arsenal | 2 - 2 | Tottenham | 1-2 | Yes | 2 | X | |
| 5 | 9/14/2019 | Tottenham | 4 - 0 | Crystal Palace | 4-0 | Yes | 1 | 1 | |
| 6 | 9/21/2019 | Leicester City | 2 - 1 | Tottenham | 0-1 | Yes | 2 | 1 | |
| 7 | 9/28/2019 | Tottenham | 2 - 1 | Southampton | 2-1 | Yes | 1 | 1 | |
| 8 | 10/5/2019 | Brighton | 3 - 0 | Tottenham | 2-0 | Yes | 1 | 1 | |
| 9 | 10/19/2019 | Tottenham | 1 - 1 | Watford | 0-1 | No | 2 | X | |
| 10 | 10/27/2019 | Liverpool | 2 - 1 | Tottenham | 0-1 | Yes | 2 | 1 | |
| 11 | 11/3/2019 | Everton | 1 - 1 | Tottenham | 0-0 | No | X | X | |
| 12 | 11/9/2019 | Tottenham | 1 - 1 | Sheffield Utd | 0-0 | No | X | X | |
| 13 | 11/23/2019 | West Ham | 2 - 3 | Tottenham | 0-2 | Yes | 2 | 2 | |
| 14 | 11/30/2019 | Tottenham | 3 - 2 | Bournemouth | 1-0 | Yes | 1 | 1 | |
| 15 | 12/4/2019 | Manchester Utd | 2 - 1 | Tottenham | 1-1 | Yes | X | 1 | |
| 16 | 12/7/2019 | Tottenham | 5 - 0 | Burnley | 3-0 | Yes | 1 | 1 | |
| 17 | 12/15/2019 | Wolverhampton | 1 - 2 | Tottenham | 0-1 | Yes | 2 | 2 | |
| 18 | 12/22/2019 | Tottenham | 0 - 2 | Chelsea | 0-2 | No | 2 | 2 | |
| 19 | 12/26/2019 | Tottenham | 2 - 1 | Brighton | 0-1 | Yes | 2 | 1 | |
| 20 | 12/28/2019 | Norwich | 2 - 2 | Tottenham | 1-0 | Yes | 1 | X | |
| 21 | 1/1/2020 | Southampton | 1 - 0 | Tottenham | 1-0 | No | 1 | 1 | |
| 22 | 1/11/2020 | Tottenham | 0 - 1 | Liverpool | 0-1 | No | 2 | 2 | |
| 23 | 1/18/2020 | Watford | 0 - 0 | Tottenham | 0-0 | No | X | X | |
| 24 | 1/22/2020 | Tottenham | 2 - 1 | Norwich | 1-0 | Yes | 1 | 1 | |
| 25 | 2/2/2020 | Tottenham | 2 - 0 | Manchester City | 0-0 | No | X | 1 | |
| 26 | 2/16/2020 | Aston Villa | 2 - 3 | Tottenham | 1-2 | Yes | 2 | 2 | |
| 27 | 2/22/2020 | Chelsea | 2 - 1 | Tottenham | 1-0 | Yes | 1 | 1 | |
| 28 | 3/1/2020 | Tottenham | 2 - 3 | Wolverhampton | 2-1 | Yes | 1 | 2 | |
| 29 | 3/7/2020 | Burnley | 1 - 1 | Tottenham | 1-0 | No | 1 | X | |
| 30 | 6/19/2020 | Tottenham | 1 - 1 | Manchester Utd | 1-0 | No | 1 | X | |
| 31 | 6/23/2020 | Tottenham | 2 - 0 | West Ham | 0-0 | No | X | 1 | |
| 32 | 7/2/2020 | Sheffield Utd | 3 - 1 | Tottenham | 1-0 | Yes | 1 | 1 | |
| 33 | 7/6/2020 | Tottenham | 1 - 0 | Everton | 1-0 | No | 1 | 1 | |
| 34 | 7/9/2020 | Bournemouth | 0 - 0 | Tottenham | 0-0 | No | X | X | |
| 35 | 7/12/2020 | Tottenham | 2 - 1 | Arsenal | 1-1 | Yes | X | 1 | |
| 36 | 7/15/2020 | Newcastle | 1 - 3 | Tottenham | 0-1 | Yes | 2 | 2 | |
| 37 | 7/19/2020 | Tottenham | 3 - 0 | Leicester City | 3-0 | Yes | 1 | 1 | |
| 38 | 7/26/2020 | Crystal Palace | 1 - 1 | Tottenham | 0-1 | No | 2 | X |