| 1 | Sat 8 Aug | 100-1 v Fleetwood TownFleetwood Town 1-0 Chesterfield | Carabao Cup First Round |
| 2 | Sat 15 Aug | 100-1 v Fleetwood TownChesterfield 0-1 Fleetwood Town | Sky Bet League Two |
| 3 | Sat 22 Aug | 101-0 v Salford CitySalford City 0-1 Chesterfield | Sky Bet League Two |
| 4 | Sat 29 Aug | 10 1-2 v Rotherham UnitedRotherham United 2-1 Chesterfield | Sky Bet League Two |
| 5 | Tue 1 Sep | 101-1 v GillinghamChesterfield 1-1 Gillingham | Sky Bet League Two |
| 6 | Sat 5 Sep | 103-3 v BarnetChesterfield 3-3 Barnet | Sky Bet League Two |
| 7 | Sat 12 Sep | 102-1 v Oldham AthleticOldham Athletic 1-2 Chesterfield | Sky Bet League Two |
| 8 | Sat 19 Sep | 102-0 v York CityChesterfield 2-0 York City | Sky Bet League Two |
| 9 | Sat 26 Sep | 101-2 v Cheltenham TownCheltenham Town 2-1 Chesterfield | Sky Bet League Two |
| 10 | Sat 3 Oct | 10 4-2 v Tranmere RoversChesterfield 4-2 Tranmere Rovers | Sky Bet League Two |
| 11 | Sat 10 Oct | 102-2 v Crawley TownCrawley Town 2-2 Chesterfield | Sky Bet League Two |
| 12 | Sat 17 Oct | 100-1 v Port ValePort Vale 1-0 Chesterfield | Sky Bet League Two |
| 13 | Tue 20 Oct | 101-1 v Colchester UnitedChesterfield 1-1 Colchester United | Sky Bet League Two |
| 14 | Sat 24 Oct | 105-1 v Crewe AlexandraChesterfield 5-1 Crewe Alexandra | Sky Bet League Two |
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