| 8.11.20162016-11-8 20:45:00 | 20:45 | EFL Trophy Southern Group A | 3. R | Portsmouth - Bristol Rovers | 1:0 (0:0) |
| 5.11.20162016-11-5 16:00:00 | 16:00 | FA Cup | 1. R | Portsmouth - Wycombe Wanderers | 1:2 (0:1) |
| 4.10.20162016-10-4 20:45:00 | 20:45 | EFL Trophy Southern Group A | 2. R | Portsmouth - Reading Academy | 5:6 (0:1) |
| 30.8.20162016-8-30 20:45:00 | 20:45 | EFL Trophy Southern Group A | 1. R | Yeovil Town - Portsmouth | 4:3 (4:2) |
| 9.8.20162016-8-9 20:45:00 | 20:45 | EFL Cup | 1. R | Coventry City - Portsmouth | 3:2 (0:1) |
| 30.1.20162016-1-30 16:00:00 | 16:00 | FA Cup | 4. R | Portsmouth - AFC Bournemouth | 1:2 (1:0) |
| 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) |