| 1 | Sat 17 Aug | 20 5-0 v Crewe AlexandraCrewe Alexandra 0-5 Chesterfield | Sky Bet League Two |
| 2 | Sat 24 Aug | 201-1 v Salford CityChesterfield 1-1 Salford City | Sky Bet League Two |
| 3 | Sat 31 Aug | 200-1 v GillinghamGillingham 1-0 Chesterfield | Sky Bet League Two |
| 4 | Tue 3 Sep | 20 1-0 v Lincoln CityLincoln City 0-1 Chesterfield | EFL Trophy Northern Group G |
| 5 | Sat 7 Sep | 202-1 v Grimsby TownChesterfield 2-1 Grimsby Town | Sky Bet League Two |
| 6 | Tue 1 Oct | 202-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 7 | Sat 5 Oct | 202-2 v WalsallChesterfield 2-2 Walsall | Sky Bet League Two |
| 8 | Fri 18 Oct | 203-0 v Newport CountyNewport County 0-3 Chesterfield | Sky Bet League Two |
| 9 | Tue 22 Oct | 201-1 v Colchester UnitedChesterfield 1-1 Colchester United | Sky Bet League Two |
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