| 1 | Fri 9 Aug | 231-1 v Swindon TownChesterfield 1-1 Swindon Town | Sky Bet League Two |
| 2 | Sat 17 Aug | 235-0 v Crewe AlexandraCrewe Alexandra 0-5 Chesterfield | Sky Bet League Two |
| 3 | Sat 24 Aug | 231-1 v Salford CityChesterfield 1-1 Salford City | Sky Bet League Two |
| 4 | Sat 31 Aug | 230-1 v GillinghamGillingham 1-0 Chesterfield | Sky Bet League Two |
| 5 | Sat 7 Sep | 232-1 v Grimsby TownChesterfield 2-1 Grimsby Town | Sky Bet League Two |
| 6 | Sat 14 Sep | 230-1 v Port ValePort Vale 1-0 Chesterfield | Sky Bet League Two |
| 7 | Sat 21 Sep | 231-1 v Cheltenham TownChesterfield 1-1 Cheltenham Town | Sky Bet League Two |
| 8 | Sat 28 Sep | 233-0 v Doncaster RoversDoncaster Rovers 0-3 Chesterfield | Sky Bet League Two |
| 9 | Tue 1 Oct | 232-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 10 | Tue 12 Nov | 233-2 v Grimsby TownChesterfield 3-2 Grimsby Town | EFL Trophy Northern Group G |
| 11 | Sat 16 Nov | 231-2 v Harrogate TownHarrogate Town 2-1 Chesterfield | Sky Bet League Two |
| 12 | Sat 23 Nov | 231-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 13 | Tue 10 Dec | 233-2 v Wigan AthleticChesterfield 3-2 Wigan Athletic | EFL Trophy Second Round |
| 14 | Tue 14 Jan | 230-0 v Rotherham UnitedChesterfield 0-0 Rotherham United | EFL Trophy Third Round |
| 15 | Sat 22 Feb | 230-1 v Swindon TownSwindon Town 1-0 Chesterfield | Sky Bet League Two |
| 16 | Sat 1 Mar | 231-3 v Crewe AlexandraChesterfield 1-3 Crewe Alexandra | Sky Bet League Two |
| 17 | Tue 4 Mar | 230-1 v Colchester UnitedColchester United 1-0 Chesterfield | Sky Bet League Two |
| 18 | Sat 8 Mar | 232-1 v Newport CountyChesterfield 2-1 Newport County | Sky Bet League Two |
| 19 | Tue 11 Mar | 234-0 v Salford CitySalford City 0-4 Chesterfield | Sky Bet League Two |
| 20 | Sat 15 Mar | 232-1 v Notts CountyNotts County 1-2 Chesterfield | Sky Bet League Two |
| 21 | Sat 22 Mar | 230-0 v Harrogate TownChesterfield 0-0 Harrogate Town | Sky Bet League Two |
| 22 | Sat 29 Mar | 231-0 v BarrowBarrow 0-1 Chesterfield | Sky Bet League Two |
| 23 | Tue 1 Apr | 232-1 v Carlisle UnitedChesterfield 2-1 Carlisle United | Sky Bet League Two |
| 24 | Sat 5 Apr | 230-4 v Tranmere RoversTranmere Rovers 4-0 Chesterfield | Sky Bet League Two |
| 25 | Tue 8 Apr | 231-1 v GillinghamChesterfield 1-1 Gillingham | Sky Bet League Two |
| 26 | Sat 12 Apr | 233-0 v Fleetwood TownChesterfield 3-0 Fleetwood Town | Sky Bet League Two |
| 27 | Fri 18 Apr | 230-0 v AFC WimbledonAFC Wimbledon 0-0 Chesterfield | Sky Bet League Two |
| 28 | Mon 21 Apr | 233-3 v Bradford CityChesterfield 3-3 Bradford City | Sky Bet League Two |
| 29 | Sat 26 Apr | 234-1 v MorecambeChesterfield 4-1 Morecambe | Sky Bet League Two |
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