| Date | League | Pos | Result | Pos | | xScore | Perf | Home | Away | Wins | Draws | Losses | Points | Pts/Game |
|---|
| 28 Feb | EFL 2 | 12 | Barnet 1 - 0 Chesterfield | 7 |  | 2 - 3  |  | | | 0/1 | 0/1 | 1/1 | 0/3 | 0.0 |
| 21 Feb | EFL 2 | 22 | Crawley Town 1 - 1 Chesterfield | 6 |  | 1 - 3 | | | | 0/2 | 1/2 | 1/2 | 1/6 | 0.5 |
| 17 Feb | EFL 2 | 8 | Chesterfield 1 - 0 Gillingham | 16 |  | 2 - 1  |  | | | 1/3 | 1/3 | 1/3 | 4/9 | 1.3 |
| 14 Feb | EFL 2 | 8 | Chesterfield 1 - 1 Harrogate Town | 24 | | 2 - 1 | | | | 1/4 | 2/4 | 1/4 | 5/12 | 1.3 |
| 7 Feb | EFL 2 | 21 | Bristol Rovers 2 - 3 Chesterfield | 11 | | 0 - 3  | | | | 2/5 | 2/5 | 1/5 | 8/15 | 1.6 |
| 31 Jan | EFL 2 | 9 | Chesterfield 2 - 2 Walsall | 4 | | 2 - 1 |  | | | 2/6 | 3/6 | 1/6 | 9/18 | 1.5 |
| 27 Jan | EFL 2 | 2 | Salford City 0 - 1 Chesterfield | 11 | | 2 - 1 | | | | 3/7 | 3/7 | 1/7 | 12/21 | 1.7 |
| 24 Jan | EFL 2 | 23 | Newport County 2 - 1 Chesterfield | 9 | | 1 - 3 | | | | 3/8 | 3/8 | 2/8 | 12/24 | 1.5 |
| 17 Jan | EFL 2 | 8 | Chesterfield 0 - 0 Bromley | 1 | | 2 - 1 | | | | 3/9 | 4/9 | 2/9 | 13/27 | 1.4 |
| 4 Jan | EFL 2 | 7 | Milton Keynes Dons 2 - 2 Chesterfield | 8 | | 2 - 2  | | | | 3/10 | 5/10 | 2/10 | 14/30 | 1.4 |
| 1 Jan | EFL 2 | 15 | Oldham Athletic 1 - 1 Chesterfield | 8 | | 1 - 3 | | | | 3/11 | 6/11 | 2/11 | 15/33 | 1.4 |
| 29 Dec | EFL 2 | 7 | Chesterfield 0 - 1 Cambridge United | 8 | | 2 - 0 | | | | 3/12 | 6/12 | 3/12 | 15/36 | 1.3 |
| 26 Dec | EFL 2 | 8 | Chesterfield 2 - 0 Notts County | 3 | | 2 - 0 | | | | 4/13 | 6/13 | 3/13 | 18/39 | 1.4 |
| 20 Dec | EFL 2 | 23 | Shrewsbury Town 0 - 1 Chesterfield | 10 | | 1 - 3 | | | | 5/14 | 6/14 | 3/14 | 21/42 | 1.5 |
| 13 Dec | EFL 2 | 12 | Chesterfield 3 - 1 Barnet | 10 | | 3 - 2 | | | | 6/15 | 6/15 | 3/15 | 24/45 | 1.6 |
| 9 Dec | EFL 2 | 7 | Cambridge United 1 - 1 Chesterfield | 12 | | 2 - 1 | | | | 6/16 | 7/16 | 3/16 | 25/48 | 1.6 |
| 29 Nov | EFL 2 | 10 | Chesterfield 1 - 2 Swindon Town | 2 | | 2 - 1 | | | | 6/17 | 7/17 | 4/17 | 25/51 | 1.5 |
| 22 Nov | EFL 2 | 8 | Crewe Alexandra 3 - 3 Chesterfield | 10 | | 2 - 1 | | | | 6/18 | 8/18 | 4/18 | 26/54 | 1.4 |
| 15 Nov | EFL 2 | 9 | Grimsby Town 0 - 1 Chesterfield | 11 | | 2 - 2 | | | | 7/19 | 8/19 | 4/19 | 29/57 | 1.5 |
| 8 Nov | EFL 2 | 7 | Chesterfield 3 - 3 Accrington Stanley | 21 | | 2 - 1 | | | | 7/20 | 9/20 | 4/20 | 30/60 | 1.5 |
| 25 Oct | EFL 2 | 18 | Tranmere Rovers 1 - 1 Chesterfield | 6 | | 1 - 3 | | | | 7/21 | 10/21 | 4/21 | 31/63 | 1.5 |
| 18 Oct | EFL 2 | 6 | Chesterfield 1 - 1 Fleetwood Town | 12 | | 3 - 1 | | | | 7/22 | 11/22 | 4/22 | 32/66 | 1.5 |
| 11 Oct | EFL 2 | 9 | Chesterfield 2 - 0 Salford City | 6 | | 2 - 1 | | | | 8/23 | 11/23 | 4/23 | 35/69 | 1.5 |
| 4 Oct | EFL 2 | 20 | Colchester United 6 - 2 Chesterfield | 6 | | 2 - 3 | | | | 8/24 | 11/24 | 5/24 | 35/72 | 1.5 |
| 27 Sep | EFL 2 | 6 | Chesterfield 4 - 1 Newport County | 22 | | 2 - 0 | | | | 9/25 | 11/25 | 5/25 | 38/75 | 1.5 |
| 20 Sep | EFL 2 | 7 | Bromley 2 - 2 Chesterfield | 6 | | 2 - 1 | | | | 9/26 | 12/26 | 5/26 | 39/78 | 1.5 |
| 13 Sep | EFL 2 | 7 | Chesterfield 1 - 1 Milton Keynes Dons | 9 | | 2 - 2 | | | | 9/27 | 13/27 | 5/27 | 40/81 | 1.5 |
| 6 Sep | EFL 2 | 6 | Walsall 1 - 0 Chesterfield | 2 | | 1 - 3 | | | | 9/28 | 13/28 | 6/28 | 40/84 | 1.4 |
| 30 Aug | EFL 2 | 2 | Chesterfield 2 - 2 Crawley Town | 22 | | 2 - 2 | | | | 9/29 | 14/29 | 6/29 | 41/87 | 1.4 |
| 23 Aug | EFL 2 | 8 | Harrogate Town 1 - 2 Chesterfield | 3 | | 1 - 3 | | | | 10/30 | 14/30 | 6/30 | 44/90 | 1.5 |
| 19 Aug | EFL 2 | 13 | Gillingham 4 - 1 Chesterfield | 2 | | 1 - 3 | | | | 10/31 | 14/31 | 7/31 | 44/93 | 1.4 |
| 16 Aug | EFL 2 | 3 | Chesterfield 3 - 1 Bristol Rovers | 20 | | - | | | | 11/32 | 14/32 | 7/32 | 47/96 | 1.5 |
| 9 Aug | EFL 2 | 19 | Cheltenham Town 0 - 2 Chesterfield | 7 | | - | | | | 12/33 | 14/33 | 7/33 | 50/99 | 1.5 |
| 2 Aug | EFL 2 | - | Chesterfield 1 - 0 Barrow | - | | - | - | | | 13/34 | 14/34 | 7/34 | 53/102 | 1.6 |