| 1 | Sat 30 Nov | 20-2 v Exeter CityExeter City 2-0 Chesterfield | Emirates FA Cup Second Round |
| 2 | Sat 7 Dec | 2 3-0 v Tranmere RoversChesterfield 3-0 Tranmere Rovers | Sky Bet League Two |
| 3 | Sat 14 Dec | 22-0 v Carlisle UnitedCarlisle United 0-2 Chesterfield | Sky Bet League Two |
| 4 | Sat 21 Dec | 21-0 v AFC WimbledonChesterfield 1-0 AFC Wimbledon | Sky Bet League Two |
| 5 | Thu 26 Dec | 20-2 v Fleetwood TownFleetwood Town 2-0 Chesterfield | Sky Bet League Two |
| 6 | Sun 29 Dec | 21-2 v Bradford CityBradford City 2-1 Chesterfield | Sky Bet League Two |
| 7 | Wed 1 Jan | 21-2 v Milton Keynes DonsChesterfield 1-2 Milton Keynes Dons | Sky Bet League Two |
| 8 | Tue 14 Jan | 20-0 v Rotherham UnitedChesterfield 0-0 Rotherham United | EFL Trophy Third Round |
| 9 | Sat 18 Jan | 21-1 v Grimsby TownGrimsby Town 1-1 Chesterfield | Sky Bet League Two |
| 10 | Sat 25 Jan | 21-1 v Port ValeChesterfield 1-1 Port Vale | Sky Bet League Two |
| 11 | Tue 28 Jan | 23-0 v BromleyChesterfield 3-0 Bromley | Sky Bet League Two |
| 12 | Sat 1 Feb | 20-1 v Cheltenham TownCheltenham Town 1-0 Chesterfield | Sky Bet League Two |
| 13 | Thu 6 Feb | 25-2 v Doncaster RoversChesterfield 5-2 Doncaster Rovers | Sky Bet League Two |
| 14 | Sat 15 Feb | 21-3 v WalsallWalsall 3-1 Chesterfield | Sky Bet League Two |
| 15 | Sat 22 Feb | 20-1 v Swindon TownSwindon Town 1-0 Chesterfield | Sky Bet League Two |
| 16 | Tue 4 Mar | 2 0-1 v Colchester UnitedColchester United 1-0 Chesterfield | Sky Bet League Two |
| 17 | Sat 8 Mar | 22-1 v Newport CountyChesterfield 2-1 Newport County | Sky Bet League Two |
| 18 | Tue 11 Mar | 24-0 v Salford CitySalford City 0-4 Chesterfield | Sky Bet League Two |
| 19 | Sat 15 Mar | 22-1 v Notts CountyNotts County 1-2 Chesterfield | Sky Bet League Two |
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