| 1 | Sat 2 Aug | 101-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 2 | Sat 9 Aug | 10 2-0 v Cheltenham TownCheltenham Town 0-2 Chesterfield | Sky Bet League Two |
| 3 | Tue 12 Aug | 100-2 v Mansfield TownChesterfield 0-2 Mansfield Town | Carabao Cup First Round |
| 4 | Sat 16 Aug | 103-1 v Bristol RoversChesterfield 3-1 Bristol Rovers | Sky Bet League Two |
| 5 | Sat 23 Aug | 102-1 v Harrogate TownHarrogate Town 1-2 Chesterfield | Sky Bet League Two |
| 6 | Sat 30 Aug | 102-2 v Crawley TownChesterfield 2-2 Crawley Town | Sky Bet League Two |
| 7 | Tue 2 Sep | 101-7 v Crewe AlexandraCrewe Alexandra 7-1 Chesterfield | EFL Trophy Northern Group H |
| 8 | Sat 6 Sep | 100-1 v WalsallWalsall 1-0 Chesterfield | Sky Bet League Two |
| 9 | Sat 13 Sep | 101-1 v Milton Keynes DonsChesterfield 1-1 Milton Keynes Dons | Sky Bet League Two |
| 10 | Sat 20 Sep | 102-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 11 | Sat 27 Sep | 104-1 v Newport CountyChesterfield 4-1 Newport County | Sky Bet League Two |
| 12 | Sat 11 Oct | 102-0 v Salford CityChesterfield 2-0 Salford City | Sky Bet League Two |
| 13 | Sat 18 Oct | 101-1 v Fleetwood TownChesterfield 1-1 Fleetwood Town | Sky Bet League Two |
| 14 | Sat 25 Oct | 101-1 v Tranmere RoversTranmere Rovers 1-1 Chesterfield | Sky Bet League Two |
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