| 1 | Sun 4 Jan | 292-2 v Milton Keynes DonsMilton Keynes Dons 2-2 Chesterfield | Sky Bet League Two |
| 2 | Sat 17 Jan | 29 0-0 v BromleyChesterfield 0-0 Bromley | Sky Bet League Two |
| 3 | Sat 24 Jan | 291-2 v Newport CountyNewport County 2-1 Chesterfield | Sky Bet League Two |
| 4 | Tue 27 Jan | 291-0 v Salford CitySalford City 0-1 Chesterfield | Sky Bet League Two |
| 5 | Sat 31 Jan | 292-2 v WalsallChesterfield 2-2 Walsall | Sky Bet League Two |
| 6 | Sat 7 Feb | 293-2 v Bristol RoversBristol Rovers 2-3 Chesterfield | Sky Bet League Two |
| 7 | Sat 14 Feb | 291-1 v Harrogate TownChesterfield 1-1 Harrogate Town | Sky Bet League Two |
| 8 | Tue 17 Feb | 291-0 v GillinghamChesterfield 1-0 Gillingham | Sky Bet League Two |
| 9 | Sat 21 Feb | 291-1 v Crawley TownCrawley Town 1-1 Chesterfield | Sky Bet League Two |
| 10 | Sat 28 Feb | 290-1 v BarnetBarnet 1-0 Chesterfield | Sky Bet League Two |
| 11 | Tue 3 Mar | 293-0 v Colchester UnitedChesterfield 3-0 Colchester United | Sky Bet League Two |
| 12 | Sat 7 Mar | 292-3 v Shrewsbury TownChesterfield 2-3 Shrewsbury Town | Sky Bet League Two |
| 13 | Sat 14 Mar | 29 3-2 v Notts CountyNotts County 2-3 Chesterfield | Sky Bet League Two |
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