| 1 | Fri 9 Aug | 81-1 v Swindon TownChesterfield 1-1 Swindon Town | Sky Bet League Two |
| 2 | Sat 17 Aug | 85-0 v Crewe AlexandraCrewe Alexandra 0-5 Chesterfield | Sky Bet League Two |
| 3 | Sat 24 Aug | 81-1 v Salford CityChesterfield 1-1 Salford City | Sky Bet League Two |
| 4 | Sat 31 Aug | 80-1 v GillinghamGillingham 1-0 Chesterfield | Sky Bet League Two |
| 5 | Tue 3 Sep | 8 1-0 v Lincoln CityLincoln City 0-1 Chesterfield | EFL Trophy Northern Group G |
| 6 | Sat 7 Sep | 8 2-1 v Grimsby TownChesterfield 2-1 Grimsby Town | Sky Bet League Two |
| 7 | Sat 21 Sep | 8 1-1 v Cheltenham TownChesterfield 1-1 Cheltenham Town | Sky Bet League Two |
| 8 | Sat 28 Sep | 83-0 v Doncaster RoversDoncaster Rovers 0-3 Chesterfield | Sky Bet League Two |
| 9 | Tue 1 Oct | 82-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 10 | Sat 5 Oct | 82-2 v WalsallChesterfield 2-2 Walsall | Sky Bet League Two |
| 11 | Sat 12 Oct | 82-2 v Notts CountyChesterfield 2-2 Notts County | Sky Bet League Two |
| 12 | Fri 18 Oct | 8 3-0 v Newport CountyNewport County 0-3 Chesterfield | Sky Bet League Two |
| 13 | Tue 22 Oct | 8 1-1 v Colchester UnitedChesterfield 1-1 Colchester United | Sky Bet League Two |
| 14 | Sat 9 Nov | 8 0-3 v Accrington StanleyChesterfield 0-3 Accrington Stanley | Sky Bet League Two |
| 15 | Tue 12 Nov | 83-2 v Grimsby TownChesterfield 3-2 Grimsby Town | EFL Trophy Northern Group G |
| 16 | Sat 16 Nov | 81-2 v Harrogate TownHarrogate Town 2-1 Chesterfield | Sky Bet League Two |
| 17 | Sat 23 Nov | 81-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 18 | Sat 30 Nov | 8 0-2 v Exeter CityExeter City 2-0 Chesterfield | Emirates FA Cup Second Round |
| 19 | Tue 3 Dec | 8 0-3 v Milton Keynes DonsMilton Keynes Dons 3-0 Chesterfield | Sky Bet League Two |
| 20 | Tue 10 Dec | 83-2 v Wigan AthleticChesterfield 3-2 Wigan Athletic | EFL Trophy Second Round |
| 21 | Sat 21 Dec | 81-0 v AFC WimbledonChesterfield 1-0 AFC Wimbledon | Sky Bet League Two |
| 22 | Thu 26 Dec | 80-2 v Fleetwood TownFleetwood Town 2-0 Chesterfield | Sky Bet League Two |
| 23 | Sun 29 Dec | 81-2 v Bradford CityBradford City 2-1 Chesterfield | Sky Bet League Two |
| 24 | Wed 1 Jan | 81-2 v Milton Keynes DonsChesterfield 1-2 Milton Keynes Dons | Sky Bet League Two |
| 25 | Tue 14 Jan | 80-0 v Rotherham UnitedChesterfield 0-0 Rotherham United | EFL Trophy Third Round |
| 26 | Sat 18 Jan | 81-1 v Grimsby TownGrimsby Town 1-1 Chesterfield | Sky Bet League Two |
| 27 | Sat 25 Jan | 81-1 v Port ValeChesterfield 1-1 Port Vale | Sky Bet League Two |
| 28 | Tue 28 Jan | 83-0 v BromleyChesterfield 3-0 Bromley | Sky Bet League Two |
| 29 | Sat 1 Feb | 80-1 v Cheltenham TownCheltenham Town 1-0 Chesterfield | Sky Bet League Two |
| 30 | Thu 6 Feb | 85-2 v Doncaster RoversChesterfield 5-2 Doncaster Rovers | Sky Bet League Two |
| 31 | Sat 15 Feb | 81-3 v WalsallWalsall 3-1 Chesterfield | Sky Bet League Two |
| 32 | Sat 1 Mar | 81-3 v Crewe AlexandraChesterfield 1-3 Crewe Alexandra | Sky Bet League Two |
| 33 | Sat 8 Mar | 82-1 v Newport CountyChesterfield 2-1 Newport County | Sky Bet League Two |
| 34 | Tue 1 Apr | 82-1 v Carlisle UnitedChesterfield 2-1 Carlisle United | Sky Bet League Two |
| 35 | Mon 21 Apr | 83-3 v Bradford CityChesterfield 3-3 Bradford City | Sky Bet League Two |
| 36 | Sat 26 Apr | 84-1 v MorecambeChesterfield 4-1 Morecambe | Sky Bet League Two |
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