| 1 | Sat 17 Aug | 245-0 v Crewe AlexandraCrewe Alexandra 0-5 Chesterfield | Sky Bet League Two |
| 2 | Sat 24 Aug | 241-1 v Salford CityChesterfield 1-1 Salford City | Sky Bet League Two |
| 3 | Sat 31 Aug | 240-1 v GillinghamGillingham 1-0 Chesterfield | Sky Bet League Two |
| 4 | Tue 3 Sep | 241-0 v Lincoln CityLincoln City 0-1 Chesterfield | EFL Trophy Northern Group G |
| 5 | Sat 7 Sep | 242-1 v Grimsby TownChesterfield 2-1 Grimsby Town | Sky Bet League Two |
| 6 | Sat 14 Sep | 240-1 v Port ValePort Vale 1-0 Chesterfield | Sky Bet League Two |
| 7 | Sat 21 Sep | 241-1 v Cheltenham TownChesterfield 1-1 Cheltenham Town | Sky Bet League Two |
| 8 | Sat 28 Sep | 243-0 v Doncaster RoversDoncaster Rovers 0-3 Chesterfield | Sky Bet League Two |
| 9 | Sat 5 Oct | 242-2 v WalsallChesterfield 2-2 Walsall | Sky Bet League Two |
| 10 | Sat 12 Oct | 242-2 v Notts CountyChesterfield 2-2 Notts County | Sky Bet League Two |
| 11 | Fri 18 Oct | 243-0 v Newport CountyNewport County 0-3 Chesterfield | Sky Bet League Two |
| 12 | Tue 22 Oct | 241-1 v Colchester UnitedChesterfield 1-1 Colchester United | Sky Bet League Two |
| 13 | Sat 9 Nov | 240-3 v Accrington StanleyChesterfield 0-3 Accrington Stanley | Sky Bet League Two |
| 14 | Sat 16 Nov | 241-2 v Harrogate TownHarrogate Town 2-1 Chesterfield | Sky Bet League Two |
| 15 | Sat 23 Nov | 241-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 16 | Tue 3 Dec | 240-3 v Milton Keynes DonsMilton Keynes Dons 3-0 Chesterfield | Sky Bet League Two |
| 17 | Sat 7 Dec | 243-0 v Tranmere RoversChesterfield 3-0 Tranmere Rovers | Sky Bet League Two |
| 18 | Tue 10 Dec | 243-2 v Wigan AthleticChesterfield 3-2 Wigan Athletic | EFL Trophy Second Round |
| 19 | Sat 14 Dec | 242-0 v Carlisle UnitedCarlisle United 0-2 Chesterfield | Sky Bet League Two |
| 20 | Sat 21 Dec | 241-0 v AFC WimbledonChesterfield 1-0 AFC Wimbledon | Sky Bet League Two |
| 21 | Thu 26 Dec | 240-2 v Fleetwood TownFleetwood Town 2-0 Chesterfield | Sky Bet League Two |
| 22 | Sun 29 Dec | 241-2 v Bradford CityBradford City 2-1 Chesterfield | Sky Bet League Two |
| 23 | Wed 1 Jan | 241-2 v Milton Keynes DonsChesterfield 1-2 Milton Keynes Dons | Sky Bet League Two |
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