| 1 | Sat 2 Aug | 201-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 2 | Sat 9 Aug | 202-0 v Cheltenham TownCheltenham Town 0-2 Chesterfield | Sky Bet League Two |
| 3 | Tue 12 Aug | 200-2 v Mansfield TownChesterfield 0-2 Mansfield Town | Carabao Cup First Round |
| 4 | Sat 16 Aug | 20 3-1 v Bristol RoversChesterfield 3-1 Bristol Rovers | Sky Bet League Two |
| 5 | Tue 19 Aug | 20 1-4 v GillinghamGillingham 4-1 Chesterfield | Sky Bet League Two |
| 6 | Sat 23 Aug | 202-1 v Harrogate TownHarrogate Town 1-2 Chesterfield | Sky Bet League Two |
| 7 | Sat 30 Aug | 202-2 v Crawley TownChesterfield 2-2 Crawley Town | Sky Bet League Two |
| 8 | Sat 6 Sep | 20 0-1 v WalsallWalsall 1-0 Chesterfield | Sky Bet League Two |
| 9 | Sat 13 Sep | 201-1 v Milton Keynes DonsChesterfield 1-1 Milton Keynes Dons | Sky Bet League Two |
| 10 | Sat 20 Sep | 20 2-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 11 | Sat 27 Sep | 204-1 v Newport CountyChesterfield 4-1 Newport County | Sky Bet League Two |
| 12 | Tue 7 Oct | 201-0 v Burton AlbionChesterfield 1-0 Burton Albion | EFL Trophy Northern Group H |
| 13 | Sat 11 Oct | 20 2-0 v Salford CityChesterfield 2-0 Salford City | Sky Bet League Two |
| 14 | Sat 25 Oct | 201-1 v Tranmere RoversTranmere Rovers 1-1 Chesterfield | Sky Bet League Two |
| 15 | Sat 1 Nov | 20 1-0 v StevenageStevenage 0-1 Chesterfield | Emirates FA Cup First Round |
| 16 | Sat 8 Nov | 203-3 v Accrington StanleyChesterfield 3-3 Accrington Stanley | Sky Bet League Two |
| 17 | Tue 11 Nov | 202-2 v Liverpool U21Chesterfield 2-2 Liverpool U21 | EFL Trophy Northern Group H |
| 18 | Sat 29 Nov | 201-2 v Swindon TownChesterfield 1-2 Swindon Town | Sky Bet League Two |
| 19 | Tue 2 Dec | 201-5 v Doncaster RoversDoncaster Rovers 5-1 Chesterfield | EFL Trophy Round of 32 |
| 20 | Sat 13 Dec | 203-1 v BarnetChesterfield 3-1 Barnet | Sky Bet League Two |
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