| 1 | Fri 9 Aug | 301-1 v Swindon TownChesterfield 1-1 Swindon Town | Sky Bet League Two |
| 2 | Sat 7 Sep | 302-1 v Grimsby TownChesterfield 2-1 Grimsby Town | Sky Bet League Two |
| 3 | Sat 14 Sep | 300-1 v Port ValePort Vale 1-0 Chesterfield | Sky Bet League Two |
| 4 | Sat 21 Sep | 30 1-1 v Cheltenham TownChesterfield 1-1 Cheltenham Town | Sky Bet League Two |
| 5 | Sat 28 Sep | 303-0 v Doncaster RoversDoncaster Rovers 0-3 Chesterfield | Sky Bet League Two |
| 6 | Sat 9 Nov | 300-3 v Accrington StanleyChesterfield 0-3 Accrington Stanley | Sky Bet League Two |
| 7 | Tue 12 Nov | 303-2 v Grimsby TownChesterfield 3-2 Grimsby Town | EFL Trophy Northern Group G |
| 8 | Sat 16 Nov | 30 1-2 v Harrogate TownHarrogate Town 2-1 Chesterfield | Sky Bet League Two |
| 9 | Sat 23 Nov | 301-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
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