| 1 | Sat 2 Aug | 91-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 2 | Sat 9 Aug | 92-0 v Cheltenham TownCheltenham Town 0-2 Chesterfield | Sky Bet League Two |
| 3 | Tue 12 Aug | 90-2 v Mansfield TownChesterfield 0-2 Mansfield Town | Carabao Cup First Round |
| 4 | Sat 16 Aug | 93-1 v Bristol RoversChesterfield 3-1 Bristol Rovers | Sky Bet League Two |
| 5 | Tue 19 Aug | 91-4 v GillinghamGillingham 4-1 Chesterfield | Sky Bet League Two |
| 6 | Sat 23 Aug | 92-1 v Harrogate TownHarrogate Town 1-2 Chesterfield | Sky Bet League Two |
| 7 | Sat 30 Aug | 92-2 v Crawley TownChesterfield 2-2 Crawley Town | Sky Bet League Two |
| 8 | Tue 2 Sep | 91-7 v Crewe AlexandraCrewe Alexandra 7-1 Chesterfield | EFL Trophy Northern Group H |
| 9 | Sat 6 Sep | 90-1 v WalsallWalsall 1-0 Chesterfield | Sky Bet League Two |
| 10 | Sat 13 Sep | 91-1 v Milton Keynes DonsChesterfield 1-1 Milton Keynes Dons | Sky Bet League Two |
| 11 | Sat 20 Sep | 92-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 12 | Sat 27 Sep | 94-1 v Newport CountyChesterfield 4-1 Newport County | Sky Bet League Two |
| 13 | Sat 4 Oct | 92-6 v Colchester UnitedColchester United 6-2 Chesterfield | Sky Bet League Two |
| 14 | Thu 1 Jan | 91-1 v Oldham AthleticOldham Athletic 1-1 Chesterfield | Sky Bet League Two |
| 15 | Sat 17 Jan | 90-0 v BromleyChesterfield 0-0 Bromley | Sky Bet League Two |
| 16 | Sat 24 Jan | 91-2 v Newport CountyNewport County 2-1 Chesterfield | Sky Bet League Two |
| 17 | Sat 31 Jan | 92-2 v WalsallChesterfield 2-2 Walsall | Sky Bet League Two |
| 18 | Sat 7 Feb | 93-2 v Bristol RoversBristol Rovers 2-3 Chesterfield | Sky Bet League Two |
| 19 | Tue 17 Feb | 91-0 v GillinghamChesterfield 1-0 Gillingham | Sky Bet League Two |
| 20 | Sat 21 Feb | 91-1 v Crawley TownCrawley Town 1-1 Chesterfield | Sky Bet League Two |
| 21 | Sat 28 Feb | 90-1 v BarnetBarnet 1-0 Chesterfield | Sky Bet League Two |
| 22 | Tue 3 Mar | 93-0 v Colchester UnitedChesterfield 3-0 Colchester United | Sky Bet League Two |
| 23 | Sat 7 Mar | 92-3 v Shrewsbury TownChesterfield 2-3 Shrewsbury Town | Sky Bet League Two |
| 24 | Sat 14 Mar | 93-2 v Notts CountyNotts County 2-3 Chesterfield | Sky Bet League Two |
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