| 1 | Tue 12 Nov | 133-2 v Grimsby TownChesterfield 3-2 Grimsby Town | EFL Trophy Northern Group G |
| 2 | Sat 18 Jan | 13 1-1 v Grimsby TownGrimsby Town 1-1 Chesterfield | Sky Bet League Two |
| 3 | Tue 28 Jan | 133-0 v BromleyChesterfield 3-0 Bromley | Sky Bet League Two |
| 4 | Sat 1 Mar | 131-3 v Crewe AlexandraChesterfield 1-3 Crewe Alexandra | Sky Bet League Two |
| 5 | Tue 4 Mar | 130-1 v Colchester UnitedColchester United 1-0 Chesterfield | Sky Bet League Two |
| 6 | Sat 8 Mar | 132-1 v Newport CountyChesterfield 2-1 Newport County | Sky Bet League Two |
| 7 | Sat 15 Mar | 132-1 v Notts CountyNotts County 1-2 Chesterfield | Sky Bet League Two |
| 8 | Sat 22 Mar | 130-0 v Harrogate TownChesterfield 0-0 Harrogate Town | Sky Bet League Two |
| 9 | Sat 29 Mar | 131-0 v BarrowBarrow 0-1 Chesterfield | Sky Bet League Two |
| 10 | Tue 1 Apr | 132-1 v Carlisle UnitedChesterfield 2-1 Carlisle United | Sky Bet League Two |
| 11 | Sat 5 Apr | 13 0-4 v Tranmere RoversTranmere Rovers 4-0 Chesterfield | Sky Bet League Two |
| 12 | Tue 8 Apr | 131-1 v GillinghamChesterfield 1-1 Gillingham | Sky Bet League Two |
| 13 | Sat 12 Apr | 133-0 v Fleetwood TownChesterfield 3-0 Fleetwood Town | Sky Bet League Two |
| 14 | Fri 18 Apr | 130-0 v AFC WimbledonAFC Wimbledon 0-0 Chesterfield | Sky Bet League Two |
| 15 | Mon 21 Apr | 133-3 v Bradford CityChesterfield 3-3 Bradford City | Sky Bet League Two |
| 16 | Sat 26 Apr | 134-1 v MorecambeChesterfield 4-1 Morecambe | Sky Bet League Two |
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