| 1 | Tue 14 Jan | 270-0 v Rotherham UnitedChesterfield 0-0 Rotherham United | EFL Trophy Third Round |
| 2 | Sat 18 Jan | 271-1 v Grimsby TownGrimsby Town 1-1 Chesterfield | Sky Bet League Two |
| 3 | Sat 25 Jan | 271-1 v Port ValeChesterfield 1-1 Port Vale | Sky Bet League Two |
| 4 | Tue 28 Jan | 273-0 v BromleyChesterfield 3-0 Bromley | Sky Bet League Two |
| 5 | Sat 1 Feb | 270-1 v Cheltenham TownCheltenham Town 1-0 Chesterfield | Sky Bet League Two |
| 6 | Thu 6 Feb | 275-2 v Doncaster RoversChesterfield 5-2 Doncaster Rovers | Sky Bet League Two |
| 7 | Sat 15 Feb | 271-3 v WalsallWalsall 3-1 Chesterfield | Sky Bet League Two |
| 8 | Sat 22 Feb | 270-1 v Swindon TownSwindon Town 1-0 Chesterfield | Sky Bet League Two |
| 9 | Sat 1 Mar | 271-3 v Crewe AlexandraChesterfield 1-3 Crewe Alexandra | Sky Bet League Two |
| 10 | Tue 4 Mar | 270-1 v Colchester UnitedColchester United 1-0 Chesterfield | Sky Bet League Two |
| 11 | Sat 8 Mar | 272-1 v Newport CountyChesterfield 2-1 Newport County | Sky Bet League Two |
| 12 | Tue 11 Mar | 274-0 v Salford CitySalford City 0-4 Chesterfield | Sky Bet League Two |
| 13 | Sat 15 Mar | 272-1 v Notts CountyNotts County 1-2 Chesterfield | Sky Bet League Two |
| 14 | Sat 22 Mar | 270-0 v Harrogate TownChesterfield 0-0 Harrogate Town | Sky Bet League Two |
| 15 | Sat 29 Mar | 271-0 v BarrowBarrow 0-1 Chesterfield | Sky Bet League Two |
| 16 | Sat 5 Apr | 270-4 v Tranmere RoversTranmere Rovers 4-0 Chesterfield | Sky Bet League Two |
| 17 | Tue 8 Apr | 271-1 v GillinghamChesterfield 1-1 Gillingham | Sky Bet League Two |
| 18 | Sat 12 Apr | 273-0 v Fleetwood TownChesterfield 3-0 Fleetwood Town | Sky Bet League Two |
| 19 | Fri 18 Apr | 270-0 v AFC WimbledonAFC Wimbledon 0-0 Chesterfield | Sky Bet League Two |
| 20 | Sat 26 Apr | 274-1 v MorecambeChesterfield 4-1 Morecambe | Sky Bet League Two |
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