| 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) |
| 11.8.20162016-8-11 20:45:00 | 20:45 | EFL Cup | 1. R | Bristol Rovers - Cardiff City | 1:0 (0:0) |
| 10.1.20162016-1-10 19:00:00 | 19:00 | FA Cup | 3. R | Cardiff City - Shrewsbury Town | 0:1 (0:0) |
| 25.8.20152015-8-25 20:50:00 | 20:50 | Capital One Cup | 2. R | Milton Keynes Dons - Cardiff City | 2:1 (0:0) |
| 11.8.20152015-8-11 20:45:00 | 20:45 | Capital One Cup | 1. R | Cardiff City - AFC Wimbledon | 1:0 (1:0) |
| 24.1.20152015-1-24 16:00:00 | 16:00 | FA Cup | 4. R | Cardiff City - Reading | 1:2 (1:0) |
| 2.1.20152015-1-2 20:45:00 | 20:45 | FA Cup | 3. R | Cardiff City - Colchester United | 3:1 (1:0) |