| 1 | Tue 3 Sep | 51-0 v Lincoln CityLincoln City 0-1 Chesterfield | EFL Trophy Northern Group G |
| 2 | Sat 7 Sep | 5 2-1 v Grimsby TownChesterfield 2-1 Grimsby Town | Sky Bet League Two |
| 3 | Sat 28 Sep | 53-0 v Doncaster RoversDoncaster Rovers 0-3 Chesterfield | Sky Bet League Two |
| 4 | Tue 1 Oct | 52-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 5 | Fri 18 Oct | 53-0 v Newport CountyNewport County 0-3 Chesterfield | Sky Bet League Two |
| 6 | Sat 9 Nov | 50-3 v Accrington StanleyChesterfield 0-3 Accrington Stanley | Sky Bet League Two |
| 7 | Tue 12 Nov | 53-2 v Grimsby TownChesterfield 3-2 Grimsby Town | EFL Trophy Northern Group G |
| 8 | Sat 16 Nov | 5 1-2 v Harrogate TownHarrogate Town 2-1 Chesterfield | Sky Bet League Two |
| 9 | Sat 23 Nov | 51-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 10 | Sat 30 Nov | 50-2 v Exeter CityExeter City 2-0 Chesterfield | Emirates FA Cup Second Round |
| 11 | Tue 3 Dec | 50-3 v Milton Keynes DonsMilton Keynes Dons 3-0 Chesterfield | Sky Bet League Two |
| 12 | Sat 7 Dec | 53-0 v Tranmere RoversChesterfield 3-0 Tranmere Rovers | Sky Bet League Two |
| 13 | Tue 10 Dec | 53-2 v Wigan AthleticChesterfield 3-2 Wigan Athletic | EFL Trophy Second Round |
| 14 | Sat 14 Dec | 5 2-0 v Carlisle UnitedCarlisle United 0-2 Chesterfield | Sky Bet League Two |
| 15 | Sat 21 Dec | 51-0 v AFC WimbledonChesterfield 1-0 AFC Wimbledon | Sky Bet League Two |
| 16 | Thu 26 Dec | 50-2 v Fleetwood TownFleetwood Town 2-0 Chesterfield | Sky Bet League Two |
| 17 | Sun 29 Dec | 51-2 v Bradford CityBradford City 2-1 Chesterfield | Sky Bet League Two |
| 18 | Wed 1 Jan | 51-2 v Milton Keynes DonsChesterfield 1-2 Milton Keynes Dons | Sky Bet League Two |
| 19 | Tue 14 Jan | 50-0 v Rotherham UnitedChesterfield 0-0 Rotherham United | EFL Trophy Third Round |
| 20 | Sat 18 Jan | 51-1 v Grimsby TownGrimsby Town 1-1 Chesterfield | Sky Bet League Two |
| 21 | Sat 25 Jan | 51-1 v Port ValeChesterfield 1-1 Port Vale | Sky Bet League Two |
| 22 | Tue 28 Jan | 53-0 v BromleyChesterfield 3-0 Bromley | Sky Bet League Two |
| 23 | Sat 1 Feb | 5 0-1 v Cheltenham TownCheltenham Town 1-0 Chesterfield | Sky Bet League Two |
| 24 | Thu 6 Feb | 55-2 v Doncaster RoversChesterfield 5-2 Doncaster Rovers | Sky Bet League Two |
| 25 | Sat 15 Feb | 51-3 v WalsallWalsall 3-1 Chesterfield | Sky Bet League Two |
| 26 | Sat 22 Feb | 50-1 v Swindon TownSwindon Town 1-0 Chesterfield | Sky Bet League Two |
| 27 | Sat 1 Mar | 51-3 v Crewe AlexandraChesterfield 1-3 Crewe Alexandra | Sky Bet League Two |
| 28 | Tue 4 Mar | 50-1 v Colchester UnitedColchester United 1-0 Chesterfield | Sky Bet League Two |
| 29 | Sat 8 Mar | 52-1 v Newport CountyChesterfield 2-1 Newport County | Sky Bet League Two |
| 30 | Tue 11 Mar | 54-0 v Salford CitySalford City 0-4 Chesterfield | Sky Bet League Two |
| 31 | Sat 15 Mar | 52-1 v Notts CountyNotts County 1-2 Chesterfield | Sky Bet League Two |
| 32 | Sat 22 Mar | 50-0 v Harrogate TownChesterfield 0-0 Harrogate Town | Sky Bet League Two |
| 33 | Sat 29 Mar | 5 1-0 v BarrowBarrow 0-1 Chesterfield | Sky Bet League Two |
| 34 | Tue 1 Apr | 52-1 v Carlisle UnitedChesterfield 2-1 Carlisle United | Sky Bet League Two |
| 35 | Sat 5 Apr | 50-4 v Tranmere RoversTranmere Rovers 4-0 Chesterfield | Sky Bet League Two |
| 36 | Tue 8 Apr | 51-1 v GillinghamChesterfield 1-1 Gillingham | Sky Bet League Two |
| 37 | Mon 21 Apr | 53-3 v Bradford CityChesterfield 3-3 Bradford City | Sky Bet League Two |
| 38 | Sat 26 Apr | 54-1 v MorecambeChesterfield 4-1 Morecambe | Sky Bet League Two |
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