| 1 | Sat 2 Aug | 4 1-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 2 | Sat 9 Aug | 42-0 v Cheltenham TownCheltenham Town 0-2 Chesterfield | Sky Bet League Two |
| 3 | Tue 12 Aug | 4 0-2 v Mansfield TownChesterfield 0-2 Mansfield Town | Carabao Cup First Round |
| 4 | Sat 16 Aug | 4 3-1 v Bristol RoversChesterfield 3-1 Bristol Rovers | Sky Bet League Two |
| 5 | Tue 19 Aug | 41-4 v GillinghamGillingham 4-1 Chesterfield | Sky Bet League Two |
| 6 | Sat 23 Aug | 42-1 v Harrogate TownHarrogate Town 1-2 Chesterfield | Sky Bet League Two |
| 7 | Sat 30 Aug | 42-2 v Crawley TownChesterfield 2-2 Crawley Town | Sky Bet League Two |
| 8 | Tue 2 Sep | 41-7 v Crewe AlexandraCrewe Alexandra 7-1 Chesterfield | EFL Trophy Northern Group H |
| 9 | Sat 6 Sep | 4 0-1 v WalsallWalsall 1-0 Chesterfield | Sky Bet League Two |
| 10 | Sat 13 Sep | 41-1 v Milton Keynes DonsChesterfield 1-1 Milton Keynes Dons | Sky Bet League Two |
| 11 | Sat 20 Sep | 4 2-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 12 | Sat 27 Sep | 44-1 v Newport CountyChesterfield 4-1 Newport County | Sky Bet League Two |
| 13 | Sat 4 Oct | 42-6 v Colchester UnitedColchester United 6-2 Chesterfield | Sky Bet League Two |
| 14 | Tue 7 Oct | 4 1-0 v Burton AlbionChesterfield 1-0 Burton Albion | EFL Trophy Northern Group H |
| 15 | Sat 11 Oct | 4 2-0 v Salford CityChesterfield 2-0 Salford City | Sky Bet League Two |
| 16 | Sat 25 Oct | 41-1 v Tranmere RoversTranmere Rovers 1-1 Chesterfield | Sky Bet League Two |
| 17 | Sat 1 Nov | 41-0 v StevenageStevenage 0-1 Chesterfield | Emirates FA Cup First Round |
| 18 | Sat 8 Nov | 43-3 v Accrington StanleyChesterfield 3-3 Accrington Stanley | Sky Bet League Two |
| 19 | Tue 11 Nov | 42-2 v Liverpool U21Chesterfield 2-2 Liverpool U21 | EFL Trophy Northern Group H |
| 20 | Sat 15 Nov | 41-0 v Grimsby TownGrimsby Town 0-1 Chesterfield | Sky Bet League Two |
| 21 | Sat 22 Nov | 43-3 v Crewe AlexandraCrewe Alexandra 3-3 Chesterfield | Sky Bet League Two |
| 22 | Sat 29 Nov | 41-2 v Swindon TownChesterfield 1-2 Swindon Town | Sky Bet League Two |
| 23 | Tue 2 Dec | 41-5 v Doncaster RoversDoncaster Rovers 5-1 Chesterfield | EFL Trophy Round of 32 |
| 24 | Sat 6 Dec | 41-2 v Doncaster RoversChesterfield 1-2 Doncaster Rovers | Emirates FA Cup Second Round |
| 25 | Tue 9 Dec | 41-1 v Cambridge UnitedCambridge United 1-1 Chesterfield | Sky Bet League Two |
| 26 | Sat 13 Dec | 43-1 v BarnetChesterfield 3-1 Barnet | Sky Bet League Two |
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