| 1 | Sat 29 Aug | 91-2 v Rotherham UnitedRotherham United 2-1 Chesterfield | Sky Bet League Two |
| 2 | Sat 5 Sep | 93-3 v BarnetChesterfield 3-3 Barnet | Sky Bet League Two |
| 3 | Sat 19 Sep | 92-0 v York CityChesterfield 2-0 York City | Sky Bet League Two |
| 4 | Tue 22 Sep | 91-1 v Port ValeChesterfield 1-1 Port Vale | EFL Trophy Northern Group D |
| 5 | Sat 26 Sep | 91-2 v Cheltenham TownCheltenham Town 2-1 Chesterfield | Sky Bet League Two |
| 6 | Tue 20 Oct | 91-1 v Colchester UnitedChesterfield 1-1 Colchester United | Sky Bet League Two |
| 7 | Sat 24 Oct | 95-1 v Crewe AlexandraChesterfield 5-1 Crewe Alexandra | Sky Bet League Two |
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