| 1 | Sat 20 Sep | 282-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 2 | Sat 4 Oct | 282-6 v Colchester UnitedColchester United 6-2 Chesterfield | Sky Bet League Two |
| 3 | Tue 7 Oct | 281-0 v Burton AlbionChesterfield 1-0 Burton Albion | EFL Trophy Northern Group H |
| 4 | Sat 11 Oct | 282-0 v Salford CityChesterfield 2-0 Salford City | Sky Bet League Two |
| 5 | Sat 18 Oct | 281-1 v Fleetwood TownChesterfield 1-1 Fleetwood Town | Sky Bet League Two |
| 6 | Sat 25 Oct | 281-1 v Tranmere RoversTranmere Rovers 1-1 Chesterfield | Sky Bet League Two |
| 7 | Sat 1 Nov | 281-0 v StevenageStevenage 0-1 Chesterfield | Emirates FA Cup First Round |
| 8 | Sat 8 Nov | 28 3-3 v Accrington StanleyChesterfield 3-3 Accrington Stanley | Sky Bet League Two |
| 9 | Tue 11 Nov | 282-2 v Liverpool U21Chesterfield 2-2 Liverpool U21 | EFL Trophy Northern Group H |
| 10 | Sat 15 Nov | 281-0 v Grimsby TownGrimsby Town 0-1 Chesterfield | Sky Bet League Two |
| 11 | Sat 22 Nov | 283-3 v Crewe AlexandraCrewe Alexandra 3-3 Chesterfield | Sky Bet League Two |
| 12 | Sat 29 Nov | 281-2 v Swindon TownChesterfield 1-2 Swindon Town | Sky Bet League Two |
| 13 | Tue 2 Dec | 281-5 v Doncaster RoversDoncaster Rovers 5-1 Chesterfield | EFL Trophy Round of 32 |
| 14 | Tue 9 Dec | 281-1 v Cambridge UnitedCambridge United 1-1 Chesterfield | Sky Bet League Two |
| 15 | Sat 13 Dec | 283-1 v BarnetChesterfield 3-1 Barnet | Sky Bet League Two |
| 16 | Sat 20 Dec | 281-0 v Shrewsbury TownShrewsbury Town 0-1 Chesterfield | Sky Bet League Two |
| 17 | Fri 26 Dec | 282-0 v Notts CountyChesterfield 2-0 Notts County | Sky Bet League Two |
| 18 | Mon 29 Dec | 280-1 v Cambridge UnitedChesterfield 0-1 Cambridge United | Sky Bet League Two |
| 19 | Thu 1 Jan | 281-1 v Oldham AthleticOldham Athletic 1-1 Chesterfield | Sky Bet League Two |
| 20 | Sun 4 Jan | 282-2 v Milton Keynes DonsMilton Keynes Dons 2-2 Chesterfield | Sky Bet League Two |
| 21 | Sat 17 Jan | 280-0 v BromleyChesterfield 0-0 Bromley | Sky Bet League Two |
| 22 | Sat 24 Jan | 281-2 v Newport CountyNewport County 2-1 Chesterfield | Sky Bet League Two |
| 23 | Sat 31 Jan | 282-2 v WalsallChesterfield 2-2 Walsall | Sky Bet League Two |
| 24 | Sat 7 Feb | 283-2 v Bristol RoversBristol Rovers 2-3 Chesterfield | Sky Bet League Two |
| 25 | Tue 17 Feb | 281-0 v GillinghamChesterfield 1-0 Gillingham | Sky Bet League Two |
| 26 | Sat 21 Feb | 281-1 v Crawley TownCrawley Town 1-1 Chesterfield | Sky Bet League Two |
| 27 | Sat 28 Feb | 280-1 v BarnetBarnet 1-0 Chesterfield | Sky Bet League Two |
| 28 | Tue 3 Mar | 283-0 v Colchester UnitedChesterfield 3-0 Colchester United | Sky Bet League Two |
| 29 | Sat 7 Mar | 282-3 v Shrewsbury TownChesterfield 2-3 Shrewsbury Town | Sky Bet League Two |
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