| 1 | Fri 9 Aug | 221-1 v Swindon TownChesterfield 1-1 Swindon Town | Sky Bet League Two |
| 2 | Sat 17 Aug | 225-0 v Crewe AlexandraCrewe Alexandra 0-5 Chesterfield | Sky Bet League Two |
| 3 | Sat 24 Aug | 221-1 v Salford CityChesterfield 1-1 Salford City | Sky Bet League Two |
| 4 | Sat 31 Aug | 22 0-1 v GillinghamGillingham 1-0 Chesterfield | Sky Bet League Two |
| 5 | Tue 3 Sep | 221-0 v Lincoln CityLincoln City 0-1 Chesterfield | EFL Trophy Northern Group G |
| 6 | Sat 14 Sep | 220-1 v Port ValePort Vale 1-0 Chesterfield | Sky Bet League Two |
| 7 | Sat 21 Sep | 221-1 v Cheltenham TownChesterfield 1-1 Cheltenham Town | Sky Bet League Two |
| 8 | Sat 28 Sep | 223-0 v Doncaster RoversDoncaster Rovers 0-3 Chesterfield | Sky Bet League Two |
| 9 | Tue 1 Oct | 222-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 10 | Sat 5 Oct | 222-2 v WalsallChesterfield 2-2 Walsall | Sky Bet League Two |
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