| 1 | Sat 2 Sep 2017 | 0-0 v Coventry CityChesterfield 0-0 Coventry City | Sky Bet League Two |
| 2 | Sat 9 Sep 2017 | 321-5 v Crewe AlexandraCrewe Alexandra 5-1 Chesterfield | Sky Bet League Two |
| 3 | Tue 12 Sep 2017 | 321-1 v Colchester UnitedColchester United 1-1 Chesterfield | Sky Bet League Two |
| 4 | Sat 23 Sep 2017 | 320-1 v Luton TownLuton Town 1-0 Chesterfield | Sky Bet League Two |
| 5 | Tue 26 Sep 2017 | 322-3 v Yeovil TownChesterfield 2-3 Yeovil Town | Sky Bet League Two |
| 6 | Sat 30 Sep 2017 | 32 0-2 v Cheltenham TownChesterfield 0-2 Cheltenham Town | Sky Bet League Two |
| 7 | Tue 17 Oct 2017 | 322-0 v Crawley TownCrawley Town 0-2 Chesterfield | Sky Bet League Two |
| 8 | Sat 21 Oct 2017 | 32 1-2 v Cambridge UnitedCambridge United 2-1 Chesterfield | Sky Bet League Two |
| 9 | Sat 28 Oct 2017 | 32 2-2 v Carlisle UnitedChesterfield 2-2 Carlisle United | Sky Bet League Two |
| 10 | Sat 11 Nov 2017 | 322-2 v Swindon TownSwindon Town 2-2 Chesterfield | Sky Bet League Two |
| 11 | Tue 5 Dec 2017 | 320-2 v Fleetwood TownFleetwood Town 2-0 Chesterfield | Checkatrade Trophy Second Round |
| 12 | Sat 9 Dec 2017 | 322-1 v BarnetChesterfield 2-1 Barnet | Sky Bet League Two |
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