| 1 | Fri 9 Aug | 41-1 v Swindon TownChesterfield 1-1 Swindon Town | Sky Bet League Two |
| 2 | Sat 17 Aug | 4 5-0 v Crewe AlexandraCrewe Alexandra 0-5 Chesterfield | Sky Bet League Two |
| 3 | Sat 24 Aug | 4 1-1 v Salford CityChesterfield 1-1 Salford City | Sky Bet League Two |
| 4 | Sat 31 Aug | 4 0-1 v GillinghamGillingham 1-0 Chesterfield | Sky Bet League Two |
| 5 | Sat 7 Sep | 42-1 v Grimsby TownChesterfield 2-1 Grimsby Town | Sky Bet League Two |
| 6 | Sat 14 Sep | 40-1 v Port ValePort Vale 1-0 Chesterfield | Sky Bet League Two |
| 7 | Sat 21 Sep | 4 1-1 v Cheltenham TownChesterfield 1-1 Cheltenham Town | Sky Bet League Two |
| 8 | Sat 28 Sep | 43-0 v Doncaster RoversDoncaster Rovers 0-3 Chesterfield | Sky Bet League Two |
| 9 | Tue 1 Oct | 42-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 10 | Sat 5 Oct | 42-2 v WalsallChesterfield 2-2 Walsall | Sky Bet League Two |
| 11 | Sat 12 Oct | 4 2-2 v Notts CountyChesterfield 2-2 Notts County | Sky Bet League Two |
| 12 | Tue 22 Oct | 41-1 v Colchester UnitedChesterfield 1-1 Colchester United | Sky Bet League Two |
| 13 | Sat 9 Nov | 4 0-3 v Accrington StanleyChesterfield 0-3 Accrington Stanley | Sky Bet League Two |
| 14 | Tue 12 Nov | 4 3-2 v Grimsby TownChesterfield 3-2 Grimsby Town | EFL Trophy Northern Group G |
| 15 | Sat 16 Nov | 4 1-2 v Harrogate TownHarrogate Town 2-1 Chesterfield | Sky Bet League Two |
| 16 | Sat 23 Nov | 41-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 17 | Sat 30 Nov | 40-2 v Exeter CityExeter City 2-0 Chesterfield | Emirates FA Cup Second Round |
| 18 | Sat 14 Dec | 42-0 v Carlisle UnitedCarlisle United 0-2 Chesterfield | Sky Bet League Two |
| 19 | Sat 21 Dec | 41-0 v AFC WimbledonChesterfield 1-0 AFC Wimbledon | Sky Bet League Two |
| 20 | Thu 26 Dec | 40-2 v Fleetwood TownFleetwood Town 2-0 Chesterfield | Sky Bet League Two |
| 21 | Sun 29 Dec | 41-2 v Bradford CityBradford City 2-1 Chesterfield | Sky Bet League Two |
| 22 | Wed 1 Jan | 41-2 v Milton Keynes DonsChesterfield 1-2 Milton Keynes Dons | Sky Bet League Two |
| 23 | Tue 14 Jan | 40-0 v Rotherham UnitedChesterfield 0-0 Rotherham United | EFL Trophy Third Round |
| 24 | Sat 18 Jan | 4 1-1 v Grimsby TownGrimsby Town 1-1 Chesterfield | Sky Bet League Two |
| 25 | Sat 25 Jan | 41-1 v Port ValeChesterfield 1-1 Port Vale | Sky Bet League Two |
| 26 | Tue 28 Jan | 43-0 v BromleyChesterfield 3-0 Bromley | Sky Bet League Two |
| 27 | Sat 1 Feb | 40-1 v Cheltenham TownCheltenham Town 1-0 Chesterfield | Sky Bet League Two |
| 28 | Thu 6 Feb | 45-2 v Doncaster RoversChesterfield 5-2 Doncaster Rovers | Sky Bet League Two |
| 29 | Sat 15 Feb | 41-3 v WalsallWalsall 3-1 Chesterfield | Sky Bet League Two |
| 30 | Sat 22 Feb | 40-1 v Swindon TownSwindon Town 1-0 Chesterfield | Sky Bet League Two |
| 31 | Tue 4 Mar | 40-1 v Colchester UnitedColchester United 1-0 Chesterfield | Sky Bet League Two |
| 32 | Sat 8 Mar | 42-1 v Newport CountyChesterfield 2-1 Newport County | Sky Bet League Two |
| 33 | Tue 11 Mar | 44-0 v Salford CitySalford City 0-4 Chesterfield | Sky Bet League Two |
| 34 | Sat 15 Mar | 42-1 v Notts CountyNotts County 1-2 Chesterfield | Sky Bet League Two |
| 35 | Sat 22 Mar | 40-0 v Harrogate TownChesterfield 0-0 Harrogate Town | Sky Bet League Two |
| 36 | Sat 29 Mar | 41-0 v BarrowBarrow 0-1 Chesterfield | Sky Bet League Two |
| 37 | Sat 5 Apr | 40-4 v Tranmere RoversTranmere Rovers 4-0 Chesterfield | Sky Bet League Two |
| 38 | Sat 12 Apr | 43-0 v Fleetwood TownChesterfield 3-0 Fleetwood Town | Sky Bet League Two |
| 39 | Fri 18 Apr | 40-0 v AFC WimbledonAFC Wimbledon 0-0 Chesterfield | Sky Bet League Two |
| 40 | Mon 21 Apr | 43-3 v Bradford CityChesterfield 3-3 Bradford City | Sky Bet League Two |
| 41 | Sat 26 Apr | 44-1 v MorecambeChesterfield 4-1 Morecambe | Sky Bet League Two |
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