| 1 | Fri 9 Aug | 101-1 v Swindon TownChesterfield 1-1 Swindon Town | Sky Bet League Two |
| 2 | Sat 17 Aug | 105-0 v Crewe AlexandraCrewe Alexandra 0-5 Chesterfield | Sky Bet League Two |
| 3 | Sat 24 Aug | 101-1 v Salford CityChesterfield 1-1 Salford City | Sky Bet League Two |
| 4 | Sat 31 Aug | 100-1 v GillinghamGillingham 1-0 Chesterfield | Sky Bet League Two |
| 5 | Tue 3 Sep | 101-0 v Lincoln CityLincoln City 0-1 Chesterfield | EFL Trophy Northern Group G |
| 6 | Sat 7 Sep | 102-1 v Grimsby TownChesterfield 2-1 Grimsby Town | Sky Bet League Two |
| 7 | Sat 14 Sep | 100-1 v Port ValePort Vale 1-0 Chesterfield | Sky Bet League Two |
| 8 | Tue 1 Oct | 102-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 9 | Sat 12 Oct | 102-2 v Notts CountyChesterfield 2-2 Notts County | Sky Bet League Two |
| 10 | Fri 18 Oct | 103-0 v Newport CountyNewport County 0-3 Chesterfield | Sky Bet League Two |
| 11 | Tue 22 Oct | 101-1 v Colchester UnitedChesterfield 1-1 Colchester United | Sky Bet League Two |
| 12 | Sat 9 Nov | 100-3 v Accrington StanleyChesterfield 0-3 Accrington Stanley | Sky Bet League Two |
| 13 | Tue 12 Nov | 103-2 v Grimsby TownChesterfield 3-2 Grimsby Town | EFL Trophy Northern Group G |
| 14 | Sat 30 Nov | 100-2 v Exeter CityExeter City 2-0 Chesterfield | Emirates FA Cup Second Round |
| 15 | Sat 1 Mar | 101-3 v Crewe AlexandraChesterfield 1-3 Crewe Alexandra | Sky Bet League Two |
| 16 | Sat 29 Mar | 101-0 v BarrowBarrow 0-1 Chesterfield | Sky Bet League Two |
| 17 | Tue 1 Apr | 102-1 v Carlisle UnitedChesterfield 2-1 Carlisle United | Sky Bet League Two |
| 18 | Sat 5 Apr | 100-4 v Tranmere RoversTranmere Rovers 4-0 Chesterfield | Sky Bet League Two |
| 19 | Sat 26 Apr | 104-1 v MorecambeChesterfield 4-1 Morecambe | Sky Bet League Two |
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