| Date | League | Pos | Result | Pos |   | xScore | Perf | Home | Away | Wins | Draws | Losses | Points | Pts/Game |
|---|
| 18 Apr | EFL 2 | 14 | Fleetwood Town 1 - 1 Chesterfield | 7 |  | 1 - 3  |  |   |  | 0/1 | 1/1 | 0/1 | 1/3 | 1.0 |
| 14 Apr | EFL 2 | 9 | Chesterfield 2 - 1 Grimsby Town | 7 |  | 2 - 2  |  |  |   | 1/2 | 1/2 | 0/2 | 4/6 | 2.0 |
| 11 Apr | EFL 2 | 8 | Chesterfield 1 - 1 Tranmere Rovers | 21 |  | 2 - 1  |  |  |   | 1/3 | 2/3 | 0/3 | 5/9 | 1.7 |
| 6 Apr | EFL 2 | 23 | Barrow 0 - 1 Chesterfield | 8 |  | 1 - 3  |  |   |  | 2/4 | 2/4 | 0/4 | 8/12 | 2.0 |
| 3 Apr | EFL 2 | 10 | Chesterfield 1 - 0 Cheltenham Town | 18 |  | 2 - 1  |  |  |   | 3/5 | 2/5 | 0/5 | 11/15 | 2.2 |
| 21 Mar | EFL 2 | 15 | Accrington Stanley 0 - 1 Chesterfield | 8 |  | 1 - 3  |  |   |  | 4/6 | 2/6 | 0/6 | 14/18 | 2.3 |
| 17 Mar | EFL 2 | 7 | Chesterfield 0 - 3 Oldham Athletic | 11 |  | 2 - 3  |  |  |   | 4/7 | 2/7 | 1/7 | 14/21 | 2.0 |
| 14 Mar | EFL 2 | 4 | Notts County 2 - 3 Chesterfield | 10 |  | 2 - 2  |  |   |  | 5/8 | 2/8 | 1/8 | 17/24 | 2.1 |
| 7 Mar | EFL 2 | 8 | Chesterfield 2 - 3 Shrewsbury Town | 17 |  | 2 - 0  |  |  |   | 5/9 | 2/9 | 2/9 | 17/27 | 1.9 |
| 3 Mar | EFL 2 | 7 | Chesterfield 3 - 0 Colchester United | 11 |  | 2 - 1  |  |  |   | 6/10 | 2/10 | 2/10 | 20/30 | 2.0 |
| 28 Feb | EFL 2 | 12 | Barnet 1 - 0 Chesterfield | 7 |  | 2 - 3  |  |   |  | 6/11 | 2/11 | 3/11 | 20/33 | 1.8 |
| 21 Feb | EFL 2 | 22 | Crawley Town 1 - 1 Chesterfield | 6 |  | 1 - 3  |  |   |  | 6/12 | 3/12 | 3/12 | 21/36 | 1.8 |
| 17 Feb | EFL 2 | 8 | Chesterfield 1 - 0 Gillingham | 16 |  | 2 - 1  |  |  |   | 7/13 | 3/13 | 3/13 | 24/39 | 1.8 |
| 14 Feb | EFL 2 | 8 | Chesterfield 1 - 1 Harrogate Town | 24 |  | 2 - 1  |  |  |   | 7/14 | 4/14 | 3/14 | 25/42 | 1.8 |
| 7 Feb | EFL 2 | 21 | Bristol Rovers 2 - 3 Chesterfield | 11 |  | 0 - 3  |  |   |  | 8/15 | 4/15 | 3/15 | 28/45 | 1.9 |
| 31 Jan | EFL 2 | 9 | Chesterfield 2 - 2 Walsall | 4 |  | 2 - 1  |  |  |   | 8/16 | 5/16 | 3/16 | 29/48 | 1.8 |
| 27 Jan | EFL 2 | 2 | Salford City 0 - 1 Chesterfield | 11 |  | 2 - 1  |  |   |  | 9/17 | 5/17 | 3/17 | 32/51 | 1.9 |
| 24 Jan | EFL 2 | 23 | Newport County 2 - 1 Chesterfield | 9 |  | 1 - 3  |  |   |  | 9/18 | 5/18 | 4/18 | 32/54 | 1.8 |
| 17 Jan | EFL 2 | 8 | Chesterfield 0 - 0 Bromley | 1 |  | 2 - 1  |  |  |   | 9/19 | 6/19 | 4/19 | 33/57 | 1.7 |
| 4 Jan | EFL 2 | 7 | Milton Keynes Dons 2 - 2 Chesterfield | 8 |  | 2 - 2  |  |   |  | 9/20 | 7/20 | 4/20 | 34/60 | 1.7 |
| 1 Jan | EFL 2 | 15 | Oldham Athletic 1 - 1 Chesterfield | 8 |  | 1 - 3  |  |   |  | 9/21 | 8/21 | 4/21 | 35/63 | 1.7 |
| 29 Dec | EFL 2 | 7 | Chesterfield 0 - 1 Cambridge United | 8 |  | 2 - 0  |  |  |   | 9/22 | 8/22 | 5/22 | 35/66 | 1.6 |
| 26 Dec | EFL 2 | 8 | Chesterfield 2 - 0 Notts County | 3 |  | 2 - 0  |  |  |   | 10/23 | 8/23 | 5/23 | 38/69 | 1.7 |
| 20 Dec | EFL 2 | 23 | Shrewsbury Town 0 - 1 Chesterfield | 10 |  | 1 - 3  |  |   |  | 11/24 | 8/24 | 5/24 | 41/72 | 1.7 |
| 13 Dec | EFL 2 | 12 | Chesterfield 3 - 1 Barnet | 10 |  | 3 - 2  |  |  |   | 12/25 | 8/25 | 5/25 | 44/75 | 1.8 |
| 9 Dec | EFL 2 | 7 | Cambridge United 1 - 1 Chesterfield | 12 |  | 2 - 1  |  |   |  | 12/26 | 9/26 | 5/26 | 45/78 | 1.7 |
| 29 Nov | EFL 2 | 10 | Chesterfield 1 - 2 Swindon Town | 2 |  | 2 - 1  |  |  |   | 12/27 | 9/27 | 6/27 | 45/81 | 1.7 |
| 22 Nov | EFL 2 | 8 | Crewe Alexandra 3 - 3 Chesterfield | 10 |  | 2 - 1  |  |   |  | 12/28 | 10/28 | 6/28 | 46/84 | 1.6 |
| 15 Nov | EFL 2 | 9 | Grimsby Town 0 - 1 Chesterfield | 11 |  | 2 - 2  |  |   |  | 13/29 | 10/29 | 6/29 | 49/87 | 1.7 |
| 8 Nov | EFL 2 | 7 | Chesterfield 3 - 3 Accrington Stanley | 21 |  | 2 - 1  |  |  |   | 13/30 | 11/30 | 6/30 | 50/90 | 1.7 |
| 25 Oct | EFL 2 | 18 | Tranmere Rovers 1 - 1 Chesterfield | 6 |  | 1 - 3  |  |   |  | 13/31 | 12/31 | 6/31 | 51/93 | 1.6 |
| 18 Oct | EFL 2 | 6 | Chesterfield 1 - 1 Fleetwood Town | 12 |  | 3 - 1  |  |  |   | 13/32 | 13/32 | 6/32 | 52/96 | 1.6 |
| 11 Oct | EFL 2 | 9 | Chesterfield 2 - 0 Salford City | 6 |  | 2 - 1  |  |  |   | 14/33 | 13/33 | 6/33 | 55/99 | 1.7 |
| 4 Oct | EFL 2 | 20 | Colchester United 6 - 2 Chesterfield | 6 |  | 2 - 3  |  |   |  | 14/34 | 13/34 | 7/34 | 55/102 | 1.6 |
| 27 Sep | EFL 2 | 6 | Chesterfield 4 - 1 Newport County | 22 |  | 2 - 0  |  |  |   | 15/35 | 13/35 | 7/35 | 58/105 | 1.7 |
| 20 Sep | EFL 2 | 7 | Bromley 2 - 2 Chesterfield | 6 |  | 2 - 1  |  |   |  | 15/36 | 14/36 | 7/36 | 59/108 | 1.6 |
| 13 Sep | EFL 2 | 7 | Chesterfield 1 - 1 Milton Keynes Dons | 9 |  | 2 - 2  |  |  |   | 15/37 | 15/37 | 7/37 | 60/111 | 1.6 |
| 6 Sep | EFL 2 | 6 | Walsall 1 - 0 Chesterfield | 2 |  | 1 - 3  |  |   |  | 15/38 | 15/38 | 8/38 | 60/114 | 1.6 |
| 30 Aug | EFL 2 | 2 | Chesterfield 2 - 2 Crawley Town | 22 |  | 2 - 2  |  |  |   | 15/39 | 16/39 | 8/39 | 61/117 | 1.6 |
| 23 Aug | EFL 2 | 8 | Harrogate Town 1 - 2 Chesterfield | 3 |  | 1 - 3  |  |   |  | 16/40 | 16/40 | 8/40 | 64/120 | 1.6 |
| 19 Aug | EFL 2 | 13 | Gillingham 4 - 1 Chesterfield | 2 |  | 1 - 3  |  |   |  | 16/41 | 16/41 | 9/41 | 64/123 | 1.6 |
| 16 Aug | EFL 2 | 3 | Chesterfield 3 - 1 Bristol Rovers | 20 |  | - |  |  |   | 17/42 | 16/42 | 9/42 | 67/126 | 1.6 |
| 9 Aug | EFL 2 | 19 | Cheltenham Town 0 - 2 Chesterfield | 7 |  | - |  |   |  | 18/43 | 16/43 | 9/43 | 70/129 | 1.6 |
| 2 Aug | EFL 2 | - | Chesterfield 1 - 0 Barrow | - |  | - | - |  |   | 19/44 | 16/44 | 9/44 | 73/132 | 1.7 |