| 1 | Sat 16 Aug | 133-1 v Bristol RoversChesterfield 3-1 Bristol Rovers | Sky Bet League Two |
| 2 | Tue 19 Aug | 131-4 v GillinghamGillingham 4-1 Chesterfield | Sky Bet League Two |
| 3 | Sat 23 Aug | 132-1 v Harrogate TownHarrogate Town 1-2 Chesterfield | Sky Bet League Two |
| 4 | Tue 2 Sep | 131-7 v Crewe AlexandraCrewe Alexandra 7-1 Chesterfield | EFL Trophy Northern Group H |
| 5 | Sat 13 Sep | 131-1 v Milton Keynes DonsChesterfield 1-1 Milton Keynes Dons | Sky Bet League Two |
| 6 | Sat 27 Sep | 13 4-1 v Newport CountyChesterfield 4-1 Newport County | Sky Bet League Two |
| 7 | Sat 4 Oct | 132-6 v Colchester UnitedColchester United 6-2 Chesterfield | Sky Bet League Two |
| 8 | Tue 7 Oct | 131-0 v Burton AlbionChesterfield 1-0 Burton Albion | EFL Trophy Northern Group H |
| 9 | Sat 1 Nov | 13 1-0 v StevenageStevenage 0-1 Chesterfield | Emirates FA Cup First Round |
| 10 | Sat 8 Nov | 13 3-3 v Accrington StanleyChesterfield 3-3 Accrington Stanley | Sky Bet League Two |
| 11 | Tue 11 Nov | 132-2 v Liverpool U21Chesterfield 2-2 Liverpool U21 | EFL Trophy Northern Group H |
| 12 | Sat 15 Nov | 131-0 v Grimsby TownGrimsby Town 0-1 Chesterfield | Sky Bet League Two |
| 13 | Sat 22 Nov | 133-3 v Crewe AlexandraCrewe Alexandra 3-3 Chesterfield | Sky Bet League Two |
| 14 | Sat 29 Nov | 131-2 v Swindon TownChesterfield 1-2 Swindon Town | Sky Bet League Two |
| 15 | Sat 6 Dec | 13 1-2 v Doncaster RoversChesterfield 1-2 Doncaster Rovers | Emirates FA Cup Second Round |
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