| 1 | Sat 2 Aug | 31-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 2 | Sat 9 Aug | 32-0 v Cheltenham TownCheltenham Town 0-2 Chesterfield | Sky Bet League Two |
| 3 | Sat 16 Aug | 33-1 v Bristol RoversChesterfield 3-1 Bristol Rovers | Sky Bet League Two |
| 4 | Tue 19 Aug | 31-4 v GillinghamGillingham 4-1 Chesterfield | Sky Bet League Two |
| 5 | Sat 30 Aug | 3 2-2 v Crawley TownChesterfield 2-2 Crawley Town | Sky Bet League Two |
| 6 | Tue 2 Sep | 31-7 v Crewe AlexandraCrewe Alexandra 7-1 Chesterfield | EFL Trophy Northern Group H |
| 7 | Sat 6 Sep | 30-1 v WalsallWalsall 1-0 Chesterfield | Sky Bet League Two |
| 8 | Sat 13 Sep | 31-1 v Milton Keynes DonsChesterfield 1-1 Milton Keynes Dons | Sky Bet League Two |
| 9 | Tue 7 Oct | 31-0 v Burton AlbionChesterfield 1-0 Burton Albion | EFL Trophy Northern Group H |
| 10 | Sat 8 Nov | 33-3 v Accrington StanleyChesterfield 3-3 Accrington Stanley | Sky Bet League Two |
| 11 | Sat 29 Nov | 31-2 v Swindon TownChesterfield 1-2 Swindon Town | Sky Bet League Two |
| 12 | Tue 2 Dec | 31-5 v Doncaster RoversDoncaster Rovers 5-1 Chesterfield | EFL Trophy Round of 32 |
| 13 | Sat 6 Dec | 31-2 v Doncaster RoversChesterfield 1-2 Doncaster Rovers | Emirates FA Cup Second Round |
| 14 | Tue 9 Dec | 31-1 v Cambridge UnitedCambridge United 1-1 Chesterfield | Sky Bet League Two |
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