| 1 | Sat 17 Aug | 65-0 v Crewe AlexandraCrewe Alexandra 0-5 Chesterfield | Sky Bet League Two |
| 2 | Sat 7 Sep | 162-1 v Grimsby TownChesterfield 2-1 Grimsby Town | Sky Bet League Two |
| 3 | Sat 14 Sep | 60-1 v Port ValePort Vale 1-0 Chesterfield | Sky Bet League Two |
| 4 | Sat 21 Sep | 61-1 v Cheltenham TownChesterfield 1-1 Cheltenham Town | Sky Bet League Two |
| 5 | Sat 28 Sep | 63-0 v Doncaster RoversDoncaster Rovers 0-3 Chesterfield | Sky Bet League Two |
| 6 | Sat 5 Oct | 62-2 v WalsallChesterfield 2-2 Walsall | Sky Bet League Two |
| 7 | Sat 12 Oct | 62-2 v Notts CountyChesterfield 2-2 Notts County | Sky Bet League Two |
| 8 | Fri 18 Oct | 6 3-0 v Newport CountyNewport County 0-3 Chesterfield | Sky Bet League Two |
| 9 | Tue 22 Oct | 61-1 v Colchester UnitedChesterfield 1-1 Colchester United | Sky Bet League Two |
| 10 | Sat 16 Nov | 61-2 v Harrogate TownHarrogate Town 2-1 Chesterfield | Sky Bet League Two |
| 11 | Sat 23 Nov | 6 1-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 12 | Tue 3 Dec | 6 0-3 v Milton Keynes DonsMilton Keynes Dons 3-0 Chesterfield | Sky Bet League Two |
| 13 | Sat 7 Dec | 6 3-0 v Tranmere RoversChesterfield 3-0 Tranmere Rovers | Sky Bet League Two |
| 14 | Tue 10 Dec | 63-2 v Wigan AthleticChesterfield 3-2 Wigan Athletic | EFL Trophy Second Round |
| 15 | Sat 14 Dec | 62-0 v Carlisle UnitedCarlisle United 0-2 Chesterfield | Sky Bet League Two |
| 16 | Sat 21 Dec | 61-0 v AFC WimbledonChesterfield 1-0 AFC Wimbledon | Sky Bet League Two |
| 17 | Thu 26 Dec | 6 0-2 v Fleetwood TownFleetwood Town 2-0 Chesterfield | Sky Bet League Two |
| 18 | Sun 29 Dec | 61-2 v Bradford CityBradford City 2-1 Chesterfield | Sky Bet League Two |
| 19 | Fri 18 Apr | 60-0 v AFC WimbledonAFC Wimbledon 0-0 Chesterfield | Sky Bet League Two |
| 20 | Mon 21 Apr | 6 3-3 v Bradford CityChesterfield 3-3 Bradford City | Sky Bet League Two |
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