| 1 | Sat 2 Aug | 11-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 2 | Sat 9 Aug | 12-0 v Cheltenham TownCheltenham Town 0-2 Chesterfield | Sky Bet League Two |
| 3 | Tue 12 Aug | 10-2 v Mansfield TownChesterfield 0-2 Mansfield Town | Carabao Cup First Round |
| 4 | Sat 16 Aug | 13-1 v Bristol RoversChesterfield 3-1 Bristol Rovers | Sky Bet League Two |
| 5 | Tue 19 Aug | 11-4 v GillinghamGillingham 4-1 Chesterfield | Sky Bet League Two |
| 6 | Sat 23 Aug | 12-1 v Harrogate TownHarrogate Town 1-2 Chesterfield | Sky Bet League Two |
| 7 | Sat 30 Aug | 12-2 v Crawley TownChesterfield 2-2 Crawley Town | Sky Bet League Two |
| 8 | Sat 6 Sep | 10-1 v WalsallWalsall 1-0 Chesterfield | Sky Bet League Two |
| 9 | Sat 13 Sep | 11-1 v Milton Keynes DonsChesterfield 1-1 Milton Keynes Dons | Sky Bet League Two |
| 10 | Sat 20 Sep | 12-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 11 | Sat 27 Sep | 14-1 v Newport CountyChesterfield 4-1 Newport County | Sky Bet League Two |
| 12 | Sat 4 Oct | 12-6 v Colchester UnitedColchester United 6-2 Chesterfield | Sky Bet League Two |
| 13 | Sat 11 Oct | 12-0 v Salford CityChesterfield 2-0 Salford City | Sky Bet League Two |
| 14 | Sat 18 Oct | 11-1 v Fleetwood TownChesterfield 1-1 Fleetwood Town | Sky Bet League Two |
| 15 | Sat 25 Oct | 11-1 v Tranmere RoversTranmere Rovers 1-1 Chesterfield | Sky Bet League Two |
| 16 | Sat 1 Nov | 11-0 v StevenageStevenage 0-1 Chesterfield | Emirates FA Cup First Round |
| 17 | Sat 8 Nov | 13-3 v Accrington StanleyChesterfield 3-3 Accrington Stanley | Sky Bet League Two |
| 18 | Sat 15 Nov | 11-0 v Grimsby TownGrimsby Town 0-1 Chesterfield | Sky Bet League Two |
| 19 | Sat 22 Nov | 1 3-3 v Crewe AlexandraCrewe Alexandra 3-3 Chesterfield | Sky Bet League Two |
| 20 | Sat 29 Nov | 11-2 v Swindon TownChesterfield 1-2 Swindon Town | Sky Bet League Two |
| 21 | Sat 6 Dec | 11-2 v Doncaster RoversChesterfield 1-2 Doncaster Rovers | Emirates FA Cup Second Round |
| 22 | Tue 9 Dec | 11-1 v Cambridge UnitedCambridge United 1-1 Chesterfield | Sky Bet League Two |
| 23 | Sat 13 Dec | 13-1 v BarnetChesterfield 3-1 Barnet | Sky Bet League Two |
| 24 | Sat 20 Dec | 11-0 v Shrewsbury TownShrewsbury Town 0-1 Chesterfield | Sky Bet League Two |
| 25 | Fri 26 Dec | 12-0 v Notts CountyChesterfield 2-0 Notts County | Sky Bet League Two |
| 26 | Mon 29 Dec | 1 0-1 v Cambridge UnitedChesterfield 0-1 Cambridge United | Sky Bet League Two |
| 27 | Thu 1 Jan | 11-1 v Oldham AthleticOldham Athletic 1-1 Chesterfield | Sky Bet League Two |
| 28 | Sun 4 Jan | 12-2 v Milton Keynes DonsMilton Keynes Dons 2-2 Chesterfield | Sky Bet League Two |
| 29 | Sat 17 Jan | 10-0 v BromleyChesterfield 0-0 Bromley | Sky Bet League Two |
| 30 | Sat 24 Jan | 11-2 v Newport CountyNewport County 2-1 Chesterfield | Sky Bet League Two |
| 31 | Tue 27 Jan | 11-0 v Salford CitySalford City 0-1 Chesterfield | Sky Bet League Two |
| 32 | Sat 31 Jan | 12-2 v WalsallChesterfield 2-2 Walsall | Sky Bet League Two |
| 33 | Sat 7 Feb | 13-2 v Bristol RoversBristol Rovers 2-3 Chesterfield | Sky Bet League Two |
| 34 | Sat 14 Feb | 11-1 v Harrogate TownChesterfield 1-1 Harrogate Town | Sky Bet League Two |
| 35 | Tue 17 Feb | 11-0 v GillinghamChesterfield 1-0 Gillingham | Sky Bet League Two |
| 36 | Sat 21 Feb | 11-1 v Crawley TownCrawley Town 1-1 Chesterfield | Sky Bet League Two |
| 37 | Sat 28 Feb | 10-1 v BarnetBarnet 1-0 Chesterfield | Sky Bet League Two |
| 38 | Tue 3 Mar | 13-0 v Colchester UnitedChesterfield 3-0 Colchester United | Sky Bet League Two |
| 39 | Sat 7 Mar | 12-3 v Shrewsbury TownChesterfield 2-3 Shrewsbury Town | Sky Bet League Two |
| 40 | Sat 14 Mar | 13-2 v Notts CountyNotts County 2-3 Chesterfield | Sky Bet League Two |
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