| 11.12.20162016-12-11 15:15:00 | 15:15 | Premier League | 15. R | Southampton - Middlesbrough | -:- |
| 5.12.20162016-12-5 21:00:00 | 21:00 | Premier League | 14. R | Middlesbrough - Hull City | -:- |
| 26.11.20162016-11-26 16:00:00 | 16:00 | Premier League | 13. R | Leicester City - Middlesbrough | 2:2 (1:1) |
| 20.11.20162016-11-20 17:00:00 | 17:00 | Premier League | 12. R | Middlesbrough - Chelsea | 0:1 (0:1) |
| 5.11.20162016-11-5 16:00:00 | 16:00 | Premier League | 11. R | Manchester City - Middlesbrough | 1:1 (1:0) |
| 29.10.20162016-10-29 16:00:00 | 16:00 | Premier League | 10. R | Middlesbrough - AFC Bournemouth | 2:0 (1:0) |
| 22.10.20162016-10-22 16:00:00 | 16:00 | Premier League | 9. R | Arsenal - Middlesbrough | 0:0 (0:0) |
| 16.10.20162016-10-16 14:30:00 | 14:30 | Premier League | 8. R | Middlesbrough - Watford | 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) |