| 1 | Sat 31 Aug | 26 0-1 v GillinghamGillingham 1-0 Chesterfield | Sky Bet League Two |
| 2 | Sat 7 Sep | 262-1 v Grimsby TownChesterfield 2-1 Grimsby Town | Sky Bet League Two |
| 3 | Sat 14 Sep | 260-1 v Port ValePort Vale 1-0 Chesterfield | Sky Bet League Two |
| 4 | Sat 21 Sep | 261-1 v Cheltenham TownChesterfield 1-1 Cheltenham Town | Sky Bet League Two |
| 5 | Tue 1 Oct | 26 2-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 6 | Sat 5 Oct | 262-2 v WalsallChesterfield 2-2 Walsall | Sky Bet League Two |
| 7 | Sat 12 Oct | 26 2-2 v Notts CountyChesterfield 2-2 Notts County | Sky Bet League Two |
| 8 | Fri 18 Oct | 263-0 v Newport CountyNewport County 0-3 Chesterfield | Sky Bet League Two |
| 9 | Tue 22 Oct | 261-1 v Colchester UnitedChesterfield 1-1 Colchester United | Sky Bet League Two |
| 10 | Sat 25 Jan | 261-1 v Port ValeChesterfield 1-1 Port Vale | Sky Bet League Two |
| 11 | Tue 28 Jan | 263-0 v BromleyChesterfield 3-0 Bromley | Sky Bet League Two |
| 12 | Thu 6 Feb | 265-2 v Doncaster RoversChesterfield 5-2 Doncaster Rovers | Sky Bet League Two |
| 13 | Sat 15 Feb | 261-3 v WalsallWalsall 3-1 Chesterfield | Sky Bet League Two |
| 14 | Sat 22 Feb | 26 0-1 v Swindon TownSwindon Town 1-0 Chesterfield | Sky Bet League Two |
| 15 | Sat 1 Mar | 261-3 v Crewe AlexandraChesterfield 1-3 Crewe Alexandra | Sky Bet League Two |
| 16 | Tue 11 Mar | 264-0 v Salford CitySalford City 0-4 Chesterfield | Sky Bet League Two |
| 17 | Sat 15 Mar | 262-1 v Notts CountyNotts County 1-2 Chesterfield | Sky Bet League Two |
| 18 | Sat 22 Mar | 260-0 v Harrogate TownChesterfield 0-0 Harrogate Town | Sky Bet League Two |
| 19 | Sat 29 Mar | 261-0 v BarrowBarrow 0-1 Chesterfield | Sky Bet League Two |
| 20 | Tue 1 Apr | 262-1 v Carlisle UnitedChesterfield 2-1 Carlisle United | Sky Bet League Two |
| 21 | Sat 5 Apr | 260-4 v Tranmere RoversTranmere Rovers 4-0 Chesterfield | Sky Bet League Two |
| 22 | Tue 8 Apr | 261-1 v GillinghamChesterfield 1-1 Gillingham | Sky Bet League Two |
| 23 | Sat 12 Apr | 263-0 v Fleetwood TownChesterfield 3-0 Fleetwood Town | Sky Bet League Two |
| 24 | Fri 18 Apr | 260-0 v AFC WimbledonAFC Wimbledon 0-0 Chesterfield | Sky Bet League Two |
| 25 | Mon 21 Apr | 263-3 v Bradford CityChesterfield 3-3 Bradford City | Sky Bet League Two |
| 26 | Sat 26 Apr | 264-1 v MorecambeChesterfield 4-1 Morecambe | Sky Bet League Two |
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