| 3.12.20162016-12-3 16:00:00 | 16:00 | Premier League | 14. R | Tottenham Hotspur - Swansea City | 5:0 (2:0) |
| 26.11.20162016-11-26 18:30:00 | 18:30 | Premier League | 13. R | Chelsea - Tottenham Hotspur | 2:1 (1:1) |
| 22.11.20162016-11-22 20:45:00 | 20:45 | Champions League grp. E | 5. R | Monaco - Tottenham Hotspur | 2:1 (0:0) |
| 19.11.20162016-11-19 18:30:00 | 18:30 | Premier League | 12. R | Tottenham Hotspur - West Ham United | 3:2 (0:1) |
| 6.11.20162016-11-6 13:00:00 | 13:00 | Premier League | 11. R | Arsenal - Tottenham Hotspur | 1:1 (1:0) |
| 2.11.20162016-11-2 20:45:00 | 20:45 | Champions League grp. E | 4. R | Tottenham Hotspur - Bayer Leverkusen | 0:1 (0:0) |
| 4.12.20162016-12-4 15:00:00 | 15:00 | FA Cup | 2. R | Bolton Wanderers - Sheffield United | 3:2 (1:0) |
| 8.11.20162016-11-8 20:45:00 | 20:45 | EFL Trophy Northern Group A | 3. R | Cheltenham Town - Bolton Wanderers | 1:0 (0:0) |
| 5.11.20162016-11-5 16:00:00 | 16:00 | FA Cup | 1. R | Bolton Wanderers - Grimsby Town | 1:0 (1:0) |
| 4.10.20162016-10-4 20:00:00 | 20:00 | EFL Trophy Northern Group A | 2. R | Bolton Wanderers - Blackpool | 1:0 (1:0) |
| 30.8.20162016-8-30 20:00:00 | 20:00 | EFL Trophy Northern Group A | 1. R | Bolton Wanderers - Everton Academy | 0:2 (0:1) |
| 9.8.20162016-8-9 20:45:00 | 20:45 | EFL Cup | 1. R | Blackpool - Bolton Wanderers | 4:2 (0:1) |