| Date | League | Pos | Result | Pos | | xScore | Perf | Home | Away | Wins | Draws | Losses | Points | Pts/Game |
|---|
| 30 Oct | EFL 2 | 16 | Newport County 4 - 1 Chesterfield | 7 |  | 2 - 3  |  | | | 0/1 | 0/1 | 1/1 | 0/3 | 0.0 |
| 24 Oct | EFL 2 | 9 | Chesterfield 5 - 1 Crewe Alexandra | 3 |  | - |  | | | 1/2 | 0/2 | 1/2 | 3/6 | 1.5 |
| 20 Oct | EFL 2 | 7 | Chesterfield 1 - 1 Colchester United | 20 |  | 2 - 1 | | | | 1/3 | 1/3 | 1/3 | 4/9 | 1.3 |
| 17 Oct | EFL 2 | 22 | Port Vale 1 - 0 Chesterfield | 7 | | 1 - 3 | | | | 1/4 | 1/4 | 2/4 | 4/12 | 1.0 |
| 10 Oct | EFL 2 | 24 | Crawley Town 2 - 2 Chesterfield | 8 | | 1 - 3 | | | | 1/5 | 2/5 | 2/5 | 5/15 | 1.0 |
| 3 Oct | EFL 2 | 11 | Chesterfield 4 - 2 Tranmere Rovers | 10 | | 2 - 1  | | | | 2/6 | 2/6 | 2/6 | 8/18 | 1.3 |
| 26 Sep | EFL 2 | 5 | Cheltenham Town 2 - 1 Chesterfield | 8 | | 2 - 2 |  | | | 2/7 | 2/7 | 3/7 | 8/21 | 1.1 |
| 19 Sep | EFL 2 | 12 | Chesterfield 2 - 0 York City | 3 | | 2 - 1 | | | | 3/8 | 2/8 | 3/8 | 11/24 | 1.4 |
| 12 Sep | EFL 2 | 10 | Oldham Athletic 1 - 2 Chesterfield | 17 | | 1 - 2  | | | | 4/9 | 2/9 | 3/9 | 14/27 | 1.6 |
| 5 Sep | EFL 2 | 16 | Chesterfield 3 - 3 Barnet | 2 | | 2 - 2 | | | | 4/10 | 3/10 | 3/10 | 15/30 | 1.5 |
| 1 Sep | EFL 2 | 16 | Chesterfield 1 - 1 Gillingham | 21 | | 2 - 0 | | | | 4/11 | 4/11 | 3/11 | 16/33 | 1.5 |
| 29 Aug | EFL 2 | 17 | Rotherham United 2 - 1 Chesterfield | 16 | | 1 - 2 | | | | 4/12 | 4/12 | 4/12 | 16/36 | 1.3 |
| 22 Aug | EFL 2 | 20 | Salford City 0 - 1 Chesterfield | 17 | | - | | | | 5/13 | 4/13 | 4/13 | 19/39 | 1.5 |
| 15 Aug | EFL 2 | - | Chesterfield 0 - 1 Fleetwood Town | - | | - | - | | | 5/14 | 4/14 | 5/14 | 19/42 | 1.4 |