| 1 | Tue 2 Sep | 301-7 v Crewe AlexandraCrewe Alexandra 7-1 Chesterfield | EFL Trophy Northern Group H |
| 2 | Sat 6 Sep | 300-1 v WalsallWalsall 1-0 Chesterfield | Sky Bet League Two |
| 3 | Sat 13 Sep | 301-1 v Milton Keynes DonsChesterfield 1-1 Milton Keynes Dons | Sky Bet League Two |
| 4 | Sat 20 Sep | 302-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 5 | Sat 27 Sep | 304-1 v Newport CountyChesterfield 4-1 Newport County | Sky Bet League Two |
| 6 | Sat 4 Oct | 302-6 v Colchester UnitedColchester United 6-2 Chesterfield | Sky Bet League Two |
| 7 | Sat 18 Oct | 30 1-1 v Fleetwood TownChesterfield 1-1 Fleetwood Town | Sky Bet League Two |
| 8 | Sat 8 Nov | 303-3 v Accrington StanleyChesterfield 3-3 Accrington Stanley | Sky Bet League Two |
| 9 | Tue 11 Nov | 302-2 v Liverpool U21Chesterfield 2-2 Liverpool U21 | EFL Trophy Northern Group H |
| 10 | Sat 15 Nov | 301-0 v Grimsby TownGrimsby Town 0-1 Chesterfield | Sky Bet League Two |
| 11 | Sat 22 Nov | 30 3-3 v Crewe AlexandraCrewe Alexandra 3-3 Chesterfield | Sky Bet League Two |
| 12 | Sat 29 Nov | 30 1-2 v Swindon TownChesterfield 1-2 Swindon Town | Sky Bet League Two |
| 13 | Sat 6 Dec | 301-2 v Doncaster RoversChesterfield 1-2 Doncaster Rovers | Emirates FA Cup Second Round |
| 14 | Tue 9 Dec | 301-1 v Cambridge UnitedCambridge United 1-1 Chesterfield | Sky Bet League Two |
| 15 | Sat 13 Dec | 303-1 v BarnetChesterfield 3-1 Barnet | Sky Bet League Two |
Football Web Pages