| 1 | Tue 14 Jan | 440-0 v Rotherham UnitedChesterfield 0-0 Rotherham United | EFL Trophy Third Round |
| 2 | Sat 25 Jan | 441-1 v Port ValeChesterfield 1-1 Port Vale | Sky Bet League Two |
| 3 | Sat 22 Feb | 44 0-1 v Swindon TownSwindon Town 1-0 Chesterfield | Sky Bet League Two |
| 4 | Sat 1 Mar | 441-3 v Crewe AlexandraChesterfield 1-3 Crewe Alexandra | Sky Bet League Two |
| 5 | Sat 8 Mar | 442-1 v Newport CountyChesterfield 2-1 Newport County | Sky Bet League Two |
| 6 | Tue 11 Mar | 444-0 v Salford CitySalford City 0-4 Chesterfield | Sky Bet League Two |
| 7 | Sat 15 Mar | 442-1 v Notts CountyNotts County 1-2 Chesterfield | Sky Bet League Two |
| 8 | Sat 22 Mar | 440-0 v Harrogate TownChesterfield 0-0 Harrogate Town | Sky Bet League Two |
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