| 1 | Fri 9 Aug | 91-1 v Swindon TownChesterfield 1-1 Swindon Town | Sky Bet League Two |
| 2 | Sat 17 Aug | 9 5-0 v Crewe AlexandraCrewe Alexandra 0-5 Chesterfield | Sky Bet League Two |
| 3 | Sat 24 Aug | 91-1 v Salford CityChesterfield 1-1 Salford City | Sky Bet League Two |
| 4 | Sat 31 Aug | 90-1 v GillinghamGillingham 1-0 Chesterfield | Sky Bet League Two |
| 5 | Tue 3 Sep | 91-0 v Lincoln CityLincoln City 0-1 Chesterfield | EFL Trophy Northern Group G |
| 6 | Sat 7 Sep | 9 2-1 v Grimsby TownChesterfield 2-1 Grimsby Town | Sky Bet League Two |
| 7 | Sat 14 Sep | 90-1 v Port ValePort Vale 1-0 Chesterfield | Sky Bet League Two |
| 8 | Sat 28 Sep | 93-0 v Doncaster RoversDoncaster Rovers 0-3 Chesterfield | Sky Bet League Two |
| 9 | Tue 1 Oct | 92-2 v BromleyBromley 2-2 Chesterfield | Sky Bet League Two |
| 10 | Sat 5 Oct | 92-2 v WalsallChesterfield 2-2 Walsall | Sky Bet League Two |
| 11 | Sat 12 Oct | 92-2 v Notts CountyChesterfield 2-2 Notts County | Sky Bet League Two |
| 12 | Fri 18 Oct | 93-0 v Newport CountyNewport County 0-3 Chesterfield | Sky Bet League Two |
| 13 | Tue 22 Oct | 91-1 v Colchester UnitedChesterfield 1-1 Colchester United | Sky Bet League Two |
| 14 | Sat 9 Nov | 90-3 v Accrington StanleyChesterfield 0-3 Accrington Stanley | Sky Bet League Two |
| 15 | Tue 12 Nov | 93-2 v Grimsby TownChesterfield 3-2 Grimsby Town | EFL Trophy Northern Group G |
| 16 | Sat 16 Nov | 9 1-2 v Harrogate TownHarrogate Town 2-1 Chesterfield | Sky Bet League Two |
| 17 | Sat 23 Nov | 91-0 v BarrowChesterfield 1-0 Barrow | Sky Bet League Two |
| 18 | Tue 3 Dec | 90-3 v Milton Keynes DonsMilton Keynes Dons 3-0 Chesterfield | Sky Bet League Two |
| 19 | Sat 7 Dec | 93-0 v Tranmere RoversChesterfield 3-0 Tranmere Rovers | Sky Bet League Two |
| 20 | Tue 10 Dec | 9 3-2 v Wigan AthleticChesterfield 3-2 Wigan Athletic | EFL Trophy Second Round |
| 21 | Sat 14 Dec | 92-0 v Carlisle UnitedCarlisle United 0-2 Chesterfield | Sky Bet League Two |
| 22 | Sat 21 Dec | 91-0 v AFC WimbledonChesterfield 1-0 AFC Wimbledon | Sky Bet League Two |
| 23 | Sat 22 Mar | 90-0 v Harrogate TownChesterfield 0-0 Harrogate Town | Sky Bet League Two |
| 24 | Sat 29 Mar | 91-0 v BarrowBarrow 0-1 Chesterfield | Sky Bet League Two |
| 25 | Tue 1 Apr | 92-1 v Carlisle UnitedChesterfield 2-1 Carlisle United | Sky Bet League Two |
| 26 | Sat 5 Apr | 90-4 v Tranmere RoversTranmere Rovers 4-0 Chesterfield | Sky Bet League Two |
| 27 | Tue 8 Apr | 91-1 v GillinghamChesterfield 1-1 Gillingham | Sky Bet League Two |
| 28 | Sat 12 Apr | 93-0 v Fleetwood TownChesterfield 3-0 Fleetwood Town | Sky Bet League Two |
| 29 | Fri 18 Apr | 90-0 v AFC WimbledonAFC Wimbledon 0-0 Chesterfield | Sky Bet League Two |
| 30 | Mon 21 Apr | 93-3 v Bradford CityChesterfield 3-3 Bradford City | Sky Bet League Two |
| 31 | Sat 26 Apr | 94-1 v MorecambeChesterfield 4-1 Morecambe | Sky Bet League Two |
Football Web Pages