| 1 | Tue 10 Dec | 112-3 v ChesterfieldChesterfield 3-2 Wigan Athletic | EFL Trophy Second Round |
| 2 | Sat 1 Feb | 34 0-1 v Cheltenham TownCheltenham Town 1-0 Chesterfield | Sky Bet League Two |
| 3 | Thu 6 Feb | 345-2 v Doncaster RoversChesterfield 5-2 Doncaster Rovers | Sky Bet League Two |
| 4 | Sat 15 Feb | 341-3 v WalsallWalsall 3-1 Chesterfield | Sky Bet League Two |
| 5 | Sat 22 Feb | 340-1 v Swindon TownSwindon Town 1-0 Chesterfield | Sky Bet League Two |
| 6 | Sat 1 Mar | 341-3 v Crewe AlexandraChesterfield 1-3 Crewe Alexandra | Sky Bet League Two |
| 7 | Tue 4 Mar | 340-1 v Colchester UnitedColchester United 1-0 Chesterfield | Sky Bet League Two |
| 8 | Tue 11 Mar | 344-0 v Salford CitySalford City 0-4 Chesterfield | Sky Bet League Two |
| 9 | Sat 22 Mar | 340-0 v Harrogate TownChesterfield 0-0 Harrogate Town | Sky Bet League Two |
| 10 | Sat 29 Mar | 341-0 v BarrowBarrow 0-1 Chesterfield | Sky Bet League Two |
| 11 | Tue 1 Apr | 342-1 v Carlisle UnitedChesterfield 2-1 Carlisle United | Sky Bet League Two |
| 12 | Sat 5 Apr | 340-4 v Tranmere RoversTranmere Rovers 4-0 Chesterfield | Sky Bet League Two |
| 13 | Tue 8 Apr | 341-1 v GillinghamChesterfield 1-1 Gillingham | Sky Bet League Two |
| 14 | Sat 12 Apr | 343-0 v Fleetwood TownChesterfield 3-0 Fleetwood Town | Sky Bet League Two |
| 15 | Fri 18 Apr | 340-0 v AFC WimbledonAFC Wimbledon 0-0 Chesterfield | Sky Bet League Two |
| 16 | Mon 21 Apr | 34 3-3 v Bradford CityChesterfield 3-3 Bradford City | Sky Bet League Two |
| 17 | Sat 26 Apr | 344-1 v MorecambeChesterfield 4-1 Morecambe | Sky Bet League Two |
| 18 | Sat 3 May | 341-0 v Accrington StanleyAccrington Stanley 0-1 Chesterfield | Sky Bet League Two |
| 19 | Sun 11 May | 34 0-2 v WalsallChesterfield 0-2 Walsall | Sky Bet League Two Play-off Semi Final |
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