| 1 | Sat 21 Sep | 331-1 v Cheltenham TownChesterfield 1-1 Cheltenham Town | Sky Bet League Two |
| 2 | Sat 28 Sep | 33 3-0 v Doncaster RoversDoncaster Rovers 0-3 Chesterfield | Sky Bet League Two |
| 3 | Tue 1 Oct | 332-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 4 | Sat 5 Oct | 332-2 v WalsallChesterfield 2-2 Walsall | Sky Bet League Two |
| 5 | Sat 12 Oct | 332-2 v Notts CountyChesterfield 2-2 Notts County | Sky Bet League Two |
| 6 | Fri 18 Oct | 333-0 v Newport CountyNewport County 0-3 Chesterfield | Sky Bet League Two |
| 7 | Tue 22 Oct | 331-1 v Colchester UnitedChesterfield 1-1 Colchester United | Sky Bet League Two |
| 8 | Sat 9 Nov | 330-3 v Accrington StanleyChesterfield 0-3 Accrington Stanley | Sky Bet League Two |
| 9 | Tue 12 Nov | 333-2 v Grimsby TownChesterfield 3-2 Grimsby Town | EFL Trophy Northern Group G |
| 10 | Sat 16 Nov | 331-2 v Harrogate TownHarrogate Town 2-1 Chesterfield | Sky Bet League Two |
| 11 | Sat 23 Nov | 331-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 12 | Sat 30 Nov | 330-2 v Exeter CityExeter City 2-0 Chesterfield | Emirates FA Cup Second Round |
| 13 | Sat 18 Jan | 331-1 v Grimsby TownGrimsby Town 1-1 Chesterfield | Sky Bet League Two |
| 14 | Sat 25 Jan | 331-1 v Port ValeChesterfield 1-1 Port Vale | Sky Bet League Two |
| 15 | Tue 28 Jan | 333-0 v BromleyChesterfield 3-0 Bromley | Sky Bet League Two |
| 16 | Sat 1 Feb | 330-1 v Cheltenham TownCheltenham Town 1-0 Chesterfield | Sky Bet League Two |
| 17 | Thu 6 Feb | 335-2 v Doncaster RoversChesterfield 5-2 Doncaster Rovers | Sky Bet League Two |
| 18 | Sat 15 Feb | 331-3 v WalsallWalsall 3-1 Chesterfield | Sky Bet League Two |
| 19 | Sat 22 Feb | 330-1 v Swindon TownSwindon Town 1-0 Chesterfield | Sky Bet League Two |
| 20 | Sat 1 Mar | 33 1-3 v Crewe AlexandraChesterfield 1-3 Crewe Alexandra | Sky Bet League Two |
| 21 | Tue 4 Mar | 33 0-1 v Colchester UnitedColchester United 1-0 Chesterfield | Sky Bet League Two |
| 22 | Sat 22 Mar | 330-0 v Harrogate TownChesterfield 0-0 Harrogate Town | Sky Bet League Two |
| 23 | Tue 1 Apr | 332-1 v Carlisle UnitedChesterfield 2-1 Carlisle United | Sky Bet League Two |
| 24 | Sat 5 Apr | 330-4 v Tranmere RoversTranmere Rovers 4-0 Chesterfield | Sky Bet League Two |
| 25 | Tue 8 Apr | 331-1 v GillinghamChesterfield 1-1 Gillingham | Sky Bet League Two |
| 26 | Sat 12 Apr | 333-0 v Fleetwood TownChesterfield 3-0 Fleetwood Town | Sky Bet League Two |
| 27 | Fri 18 Apr | 330-0 v AFC WimbledonAFC Wimbledon 0-0 Chesterfield | Sky Bet League Two |
| 28 | Mon 21 Apr | 333-3 v Bradford CityChesterfield 3-3 Bradford City | Sky Bet League Two |
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