| 1 | Sat 2 Aug | 81-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 2 | Sat 9 Aug | 82-0 v Cheltenham TownCheltenham Town 0-2 Chesterfield | Sky Bet League Two |
| 3 | Tue 12 Aug | 80-2 v Mansfield TownChesterfield 0-2 Mansfield Town | Carabao Cup First Round |
| 4 | Sat 16 Aug | 83-1 v Bristol RoversChesterfield 3-1 Bristol Rovers | Sky Bet League Two |
| 5 | Tue 19 Aug | 81-4 v GillinghamGillingham 4-1 Chesterfield | Sky Bet League Two |
| 6 | Sat 23 Aug | 82-1 v Harrogate TownHarrogate Town 1-2 Chesterfield | Sky Bet League Two |
| 7 | Sat 30 Aug | 82-2 v Crawley TownChesterfield 2-2 Crawley Town | Sky Bet League Two |
| 8 | Tue 2 Sep | 81-7 v Crewe AlexandraCrewe Alexandra 7-1 Chesterfield | EFL Trophy Northern Group H |
| 9 | Sat 6 Sep | 80-1 v WalsallWalsall 1-0 Chesterfield | Sky Bet League Two |
| 10 | Sat 20 Sep | 82-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 11 | Sat 27 Sep | 8 4-1 v Newport CountyChesterfield 4-1 Newport County | Sky Bet League Two |
| 12 | Sat 4 Oct | 82-6 v Colchester UnitedColchester United 6-2 Chesterfield | Sky Bet League Two |
| 13 | Tue 7 Oct | 81-0 v Burton AlbionChesterfield 1-0 Burton Albion | EFL Trophy Northern Group H |
| 14 | Sat 11 Oct | 82-0 v Salford CityChesterfield 2-0 Salford City | Sky Bet League Two |
| 15 | Sat 18 Oct | 81-1 v Fleetwood TownChesterfield 1-1 Fleetwood Town | Sky Bet League Two |
| 16 | Sat 25 Oct | 8 1-1 v Tranmere RoversTranmere Rovers 1-1 Chesterfield | Sky Bet League Two |
| 17 | Sat 6 Dec | 81-2 v Doncaster RoversChesterfield 1-2 Doncaster Rovers | Emirates FA Cup Second Round |
| 18 | Tue 9 Dec | 81-1 v Cambridge UnitedCambridge United 1-1 Chesterfield | Sky Bet League Two |
| 19 | Sat 13 Dec | 8 3-1 v BarnetChesterfield 3-1 Barnet | Sky Bet League Two |
| 20 | Sat 20 Dec | 81-0 v Shrewsbury TownShrewsbury Town 0-1 Chesterfield | Sky Bet League Two |
| 21 | Fri 26 Dec | 82-0 v Notts CountyChesterfield 2-0 Notts County | Sky Bet League Two |
| 22 | Mon 29 Dec | 80-1 v Cambridge UnitedChesterfield 0-1 Cambridge United | Sky Bet League Two |
| 23 | Thu 1 Jan | 81-1 v Oldham AthleticOldham Athletic 1-1 Chesterfield | Sky Bet League Two |
| 24 | Sun 4 Jan | 82-2 v Milton Keynes DonsMilton Keynes Dons 2-2 Chesterfield | Sky Bet League Two |
| 25 | Sat 17 Jan | 80-0 v BromleyChesterfield 0-0 Bromley | Sky Bet League Two |
| 26 | Sat 24 Jan | 81-2 v Newport CountyNewport County 2-1 Chesterfield | Sky Bet League Two |
| 27 | Tue 27 Jan | 8 1-0 v Salford CitySalford City 0-1 Chesterfield | Sky Bet League Two |
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