| 1 | Sat 6 Sep | 250-1 v WalsallWalsall 1-0 Chesterfield | Sky Bet League Two |
| 2 | Sat 13 Sep | 251-1 v Milton Keynes DonsChesterfield 1-1 Milton Keynes Dons | Sky Bet League Two |
| 3 | Sat 20 Sep | 252-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 4 | Sat 27 Sep | 254-1 v Newport CountyChesterfield 4-1 Newport County | Sky Bet League Two |
| 5 | Sat 4 Oct | 252-6 v Colchester UnitedColchester United 6-2 Chesterfield | Sky Bet League Two |
| 6 | Tue 7 Oct | 251-0 v Burton AlbionChesterfield 1-0 Burton Albion | EFL Trophy Northern Group H |
| 7 | Tue 11 Nov | 252-2 v Liverpool U21Chesterfield 2-2 Liverpool U21 | EFL Trophy Northern Group H |
| 8 | Sat 29 Nov | 251-2 v Swindon TownChesterfield 1-2 Swindon Town | Sky Bet League Two |
| 9 | Tue 2 Dec | 251-5 v Doncaster RoversDoncaster Rovers 5-1 Chesterfield | EFL Trophy Round of 32 |
| 10 | Tue 9 Dec | 251-1 v Cambridge UnitedCambridge United 1-1 Chesterfield | Sky Bet League Two |
| 11 | Sat 13 Dec | 253-1 v BarnetChesterfield 3-1 Barnet | Sky Bet League Two |
| 12 | Sat 20 Dec | 251-0 v Shrewsbury TownShrewsbury Town 0-1 Chesterfield | Sky Bet League Two |
| 13 | Fri 26 Dec | 252-0 v Notts CountyChesterfield 2-0 Notts County | Sky Bet League Two |
| 14 | Mon 29 Dec | 250-1 v Cambridge UnitedChesterfield 0-1 Cambridge United | Sky Bet League Two |
| 15 | Thu 1 Jan | 251-1 v Oldham AthleticOldham Athletic 1-1 Chesterfield | Sky Bet League Two |
| 16 | Sat 17 Jan | 250-0 v BromleyChesterfield 0-0 Bromley | Sky Bet League Two |
| 17 | Tue 27 Jan | 251-0 v Salford CitySalford City 0-1 Chesterfield | Sky Bet League Two |
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