| 6.12.20162016-12-6 20:45:00 | 20:45 | EFL Trophy Final Stage | 2. R | Scunthorpe United - Morecambe | -:- |
| 8.11.20162016-11-8 20:45:00 | 20:45 | EFL Trophy Northern Group G | 3. R | Cambridge United - Scunthorpe United | 0:2 (0:1) |
| 5.11.20162016-11-5 16:00:00 | 16:00 | FA Cup | 1. R | Charlton Athletic - Scunthorpe United | 3:1 (2:0) |
| 4.10.20162016-10-4 20:45:00 | 20:45 | EFL Trophy Northern Group G | 2. R | Scunthorpe United - Shrewsbury Town | 2:0 (1:0) |
| 30.8.20162016-8-30 20:45:00 | 20:45 | EFL Trophy Northern Group G | 1. R | Scunthorpe United - Middlesbrough Academy | 2:1 (0:0) |
| 23.8.20162016-8-23 20:45:00 | 20:45 | EFL Cup | 2. R | Scunthorpe United - Bristol City | 1:2 (0:1) |
| 9.8.20162016-8-9 20:45:00 | 20:45 | EFL Cup | 1. R | Scunthorpe United - Notts County | 2:0 (0:0) |
| 6.12.20162016-12-6 20:30:00 | 20:30 | EFL Trophy Final Stage | 2. R | Rochdale - Chesterfield | -:- |
| 3.12.20162016-12-3 16:05:00 | 16:05 | FA Cup | 2. R | Chesterfield - Wycombe Wanderers | 0:5 (0:2) |
| 8.11.20162016-11-8 20:30:00 | 20:30 | EFL Trophy Northern Group B | 3. R | Crewe Alexandra - Chesterfield | 0:2 (0:1) |
| 5.11.20162016-11-5 16:00:00 | 16:00 | FA Cup | 1. R | Colchester United - Chesterfield | 1:2 (0:1) |
| 4.10.20162016-10-4 20:45:00 | 20:45 | EFL Trophy Northern Group B | 2. R | Chesterfield - Accrington Stanley | 1:4 (0:3) |
| 30.8.20162016-8-30 20:45:00 | 20:45 | EFL Trophy Northern Group B | 1. R | Chesterfield - Wolverhampton Wanderers Academy | 2:1 (1:0) |
| 9.8.20162016-8-9 20:45:00 | 20:45 | EFL Cup | 1. R | Rochdale - Chesterfield | 3:1 (0:1) |