| 1 | Tue 3 Sep | 11-0 v Lincoln CityLincoln City 0-1 Chesterfield | EFL Trophy Northern Group G |
| 2 | Sat 5 Oct | 12-2 v WalsallChesterfield 2-2 Walsall | Sky Bet League Two |
| 3 | Sat 12 Oct | 12-2 v Notts CountyChesterfield 2-2 Notts County | Sky Bet League Two |
| 4 | Fri 18 Oct | 13-0 v Newport CountyNewport County 0-3 Chesterfield | Sky Bet League Two |
| 5 | Tue 22 Oct | 11-1 v Colchester UnitedChesterfield 1-1 Colchester United | Sky Bet League Two |
| 6 | Sat 9 Nov | 10-3 v Accrington StanleyChesterfield 0-3 Accrington Stanley | Sky Bet League Two |
| 7 | Sat 30 Nov | 10-2 v Exeter CityExeter City 2-0 Chesterfield | Emirates FA Cup Second Round |
| 8 | Tue 3 Dec | 10-3 v Milton Keynes DonsMilton Keynes Dons 3-0 Chesterfield | Sky Bet League Two |
| 9 | Sat 7 Dec | 13-0 v Tranmere RoversChesterfield 3-0 Tranmere Rovers | Sky Bet League Two |
| 10 | Sat 14 Dec | 12-0 v Carlisle UnitedCarlisle United 0-2 Chesterfield | Sky Bet League Two |
| 11 | Sat 21 Dec | 11-0 v AFC WimbledonChesterfield 1-0 AFC Wimbledon | Sky Bet League Two |
| 12 | Thu 26 Dec | 10-2 v Fleetwood TownFleetwood Town 2-0 Chesterfield | Sky Bet League Two |
| 13 | Sun 29 Dec | 11-2 v Bradford CityBradford City 2-1 Chesterfield | Sky Bet League Two |
| 14 | Wed 1 Jan | 11-2 v Milton Keynes DonsChesterfield 1-2 Milton Keynes Dons | Sky Bet League Two |
| 15 | Sat 18 Jan | 11-1 v Grimsby TownGrimsby Town 1-1 Chesterfield | Sky Bet League Two |
| 16 | Sat 25 Jan | 11-1 v Port ValeChesterfield 1-1 Port Vale | Sky Bet League Two |
| 17 | Tue 28 Jan | 13-0 v BromleyChesterfield 3-0 Bromley | Sky Bet League Two |
| 18 | Sat 1 Feb | 10-1 v Cheltenham TownCheltenham Town 1-0 Chesterfield | Sky Bet League Two |
| 19 | Thu 6 Feb | 15-2 v Doncaster RoversChesterfield 5-2 Doncaster Rovers | Sky Bet League Two |
| 20 | Sat 15 Feb | 11-3 v WalsallWalsall 3-1 Chesterfield | Sky Bet League Two |
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