The 2019/20 season was one to forget for Tottenham, despite Jose Mourinho coming in to replace Mauricio Pochettino as manager 12 games in after Spurs dropped to 14th place, winning just 3 of their first 12 games.
Things improved but they could still only manage a 6th place finish, tied with Wolves but ahead on goal difference. Stats provider Opta revealed that Tottenham had taken the least number of shots all season since records began in 1997.
Their Champions League bid ended in the Round of 16, Norwich beat them on penalties in the 5th Round of the FA Cup, and lowly Colchester sent them flying out of the EFL Cup early on in the 3rd Round. Their win ratio for all games played was a shockingly low 40.38%.
| Date | Competition | Home | HG | AG | Away |
|---|---|---|---|---|---|
| 10/08/2019 | Premier League | Tottenham | 3 | 1 | Aston Villa |
| 17/08/2019 | Premier League | Manchester City | 2 | 2 | Tottenham |
| 25/08/2019 | Premier League | Tottenham | 0 | 1 | Newcastle Utd |
| 01/09/2019 | Premier League | Arsenal | 2 | 2 | Tottenham |
| 14/09/2019 | Premier League | Tottenham | 4 | 0 | Crystal Palace |
| 18/09/2019 | Champions League | Olympiacos | 2 | 2 | Tottenham |
| 21/09/2019 | Premier League | Leicester City | 2 | 1 | Tottenham |
| 24/09/2019 | EFL Cup | Colchester Utd | 0 (4) | 0 (3) | Tottenham |
| 28/09/2019 | Premier League | Tottenham | 2 | 1 | Southampton |
| 01/10/2019 | Champions League | Tottenham | 2 | 7 | Bayern Munich |
| 05/10/2019 | Premier League | Brighton | 3 | 0 | Tottenham |
| 19/10/2019 | Premier League | Tottenham | 1 | 1 | Watford |
| 22/10/2019 | Champions League | Tottenham | 5 | 0 | Red Star |
| 27/10/2019 | Premier League | Liverpool | 2 | 1 | Tottenham |
| 03/11/2019 | Premier League | Everton | 1 | 1 | Tottenham |
| 06/11/2019 | Champions League | Red Star | 0 | 4 | Tottenham |
| 09/11/2019 | Premier League | Tottenham | 1 | 1 | Sheffield Utd |
| 23/11/2019 | Premier League | West Ham | 2 | 3 | Tottenham |
| 26/11/2019 | Champions League | Tottenham | 4 | 2 | Olympiacos |
| 30/11/2019 | Premier League | Tottenham | 3 | 2 | Bournemouth |
| 04/12/2019 | Premier League | Manchester Utd | 2 | 1 | Tottenham |
| 07/12/2019 | Premier League | Tottenham | 5 | 0 | Burnley |
| 11/12/2019 | Champions League | Bayern Munich | 3 | 1 | Tottenham |
| 15/12/2019 | Premier League | Wolves | 1 | 2 | Tottenham |
| 22/12/2019 | Premier League | Tottenham | 0 | 2 | Chelsea |
| 26/12/2019 | Premier League | Tottenham | 2 | 1 | Brighton |
| 28/12/2019 | Premier League | Norwich City | 2 | 2 | Tottenham |
| 01/01/2020 | Premier League | Southampton | 1 | 0 | Tottenham |
| 05/01/2020 | FA Cup | Middlesbrough | 1 | 1 | Tottenham |
| 11/01/2020 | Premier League | Tottenham | 0 | 1 | Liverpool |
| 14/01/2020 | FA Cup | Tottenham | 2 | 1 | Middlesbrough |
| 18/01/2020 | Premier League | Watford | 0 | 0 | Tottenham |
| 22/01/2020 | Premier League | Tottenham | 2 | 1 | Norwich City |
| 25/01/2020 | FA Cup | Southampton | 1 | 1 | Tottenham |
| 02/02/2020 | Premier League | Tottenham | 2 | 0 | Manchester City |
| 05/02/2020 | FA Cup | Tottenham | 3 | 2 | Southampton |
| 16/02/2020 | Premier League | Aston Villa | 2 | 3 | Tottenham |
| 19/02/2020 | Champions League | Tottenham | 0 | 1 | RB Leipzig |
| 22/02/2020 | Premier League | Chelsea | 2 | 1 | Tottenham |
| 01/03/2020 | Premier League | Tottenham | 2 | 3 | Wolves |
| 04/03/2020 | FA Cup | Tottenham | 1 (2) | 1 (3) | Norwich City |
| 07/03/2020 | Premier League | Burnley | 1 | 1 | Tottenham |
| 10/03/2020 | Champions League | RB Leipzig | 3 | 0 | Tottenham |
| 19/06/2020 | Premier League | Tottenham | 1 | 1 | Manchester Utd |
| 23/06/2020 | Premier League | Tottenham | 2 | 0 | West Ham |
| 02/07/2020 | Premier League | Sheffield Utd | 3 | 1 | Tottenham |
| 06/07/2020 | Premier League | Tottenham | 1 | 0 | Everton |
| 09/07/2020 | Premier League | Bournemouth | 0 | 0 | Tottenham |
| 12/07/2020 | Premier League | Tottenham | 2 | 1 | Arsenal |
| 15/07/2020 | Premier League | Newcastle Utd | 1 | 3 | Tottenham |
| 19/07/2020 | Premier League | Tottenham | 3 | 0 | Leicester City |
| 26/07/2020 | Premier League | Crystal Palace | 1 | 1 | Tottenham |