| Date | League | Pos | Result | Pos |   | xScore | Perf | Home | Away | Wins | Draws | Losses | Points | Pts/Game |
|---|
| 9 Dec | EFL 2 | 7 | Cambridge United 1 - 1 Chesterfield | 12 |  | 2 - 1  |  |   |  | 0/1 | 1/1 | 0/1 | 1/3 | 1.0 |
| 29 Nov | EFL 2 | 10 | Chesterfield 1 - 2 Swindon Town | 2 |  | 2 - 1  |  |  |   | 0/2 | 1/2 | 1/2 | 1/6 | 0.5 |
| 22 Nov | EFL 2 | 8 | Crewe Alexandra 3 - 3 Chesterfield | 10 |  | 2 - 1  |  |   |  | 0/3 | 2/3 | 1/3 | 2/9 | 0.7 |
| 8 Nov | EFL 2 | 7 | Chesterfield 3 - 3 Accrington Stanley | 21 |  | 2 - 1  |  |  |   | 0/4 | 3/4 | 1/4 | 3/12 | 0.8 |
| 25 Oct | EFL 2 | 18 | Tranmere Rovers 1 - 1 Chesterfield | 6 |  | 1 - 3  |  |   |  | 0/5 | 4/5 | 1/5 | 4/15 | 0.8 |
| 18 Oct | EFL 2 | 6 | Chesterfield 1 - 1 Fleetwood Town | 12 |  | 3 - 1  |  |  |   | 0/6 | 5/6 | 1/6 | 5/18 | 0.8 |
| 11 Oct | EFL 2 | 9 | Chesterfield 2 - 0 Salford City | 6 |  | 2 - 1  |  |  |   | 1/7 | 5/7 | 1/7 | 8/21 | 1.1 |
| 4 Oct | EFL 2 | 20 | Colchester United 6 - 2 Chesterfield | 6 |  | 2 - 3  |  |   |  | 1/8 | 5/8 | 2/8 | 8/24 | 1.0 |
| 27 Sep | EFL 2 | 6 | Chesterfield 4 - 1 Newport County | 22 |  | 2 - 0  |  |  |   | 2/9 | 5/9 | 2/9 | 11/27 | 1.2 |
| 20 Sep | EFL 2 | 7 | Bromley 2 - 2 Chesterfield | 6 |  | 2 - 1  |  |   |  | 2/10 | 6/10 | 2/10 | 12/30 | 1.2 |
| 13 Sep | EFL 2 | 7 | Chesterfield 1 - 1 Milton Keynes Dons | 9 |  | 2 - 2  |  |  |   | 2/11 | 7/11 | 2/11 | 13/33 | 1.2 |
| 6 Sep | EFL 2 | 6 | Walsall 1 - 0 Chesterfield | 2 |  | 1 - 3  |  |   |  | 2/12 | 7/12 | 3/12 | 13/36 | 1.1 |
| 30 Aug | EFL 2 | 2 | Chesterfield 2 - 2 Crawley Town | 22 |  | 2 - 2  |  |  |   | 2/13 | 8/13 | 3/13 | 14/39 | 1.1 |
| 23 Aug | EFL 2 | 8 | Harrogate Town 1 - 2 Chesterfield | 3 |  | 1 - 3  |  |   |  | 3/14 | 8/14 | 3/14 | 17/42 | 1.2 |
| 19 Aug | EFL 2 | 13 | Gillingham 4 - 1 Chesterfield | 2 |  | 1 - 3  |  |   |  | 3/15 | 8/15 | 4/15 | 17/45 | 1.1 |
| 16 Aug | EFL 2 | 3 | Chesterfield 3 - 1 Bristol Rovers | 20 |  | - |  |  |   | 4/16 | 8/16 | 4/16 | 20/48 | 1.3 |
| 9 Aug | EFL 2 | 19 | Cheltenham Town 0 - 2 Chesterfield | 7 |  | - |  |   |  | 5/17 | 8/17 | 4/17 | 23/51 | 1.4 |
| 2 Aug | EFL 2 | - | Chesterfield 1 - 0 Barrow | - |  | - | - |  |   | 6/18 | 8/18 | 4/18 | 26/54 | 1.4 |