| 1 | Sat 5 Aug 2017 | 111-3 v Grimsby TownChesterfield 1-3 Grimsby Town | Sky Bet League Two |
| 2 | Tue 8 Aug 2017 | 111-4 v Sheffield WednesdaySheffield Wednesday 4-1 Chesterfield | Carabao Cup First Round |
| 3 | Sat 12 Aug 2017 | 11 0-2 v Notts CountyNotts County 2-0 Chesterfield | Sky Bet League Two |
| 4 | Sat 19 Aug 2017 | 112-0 v Port ValeChesterfield 2-0 Port Vale | Sky Bet League Two |
| 5 | Tue 29 Aug 2017 | 11 2-4 v Bradford CityChesterfield 2-4 Bradford City | Checkatrade Trophy Northern Group F |
| 6 | Sat 2 Sep 2017 | 110-0 v Coventry CityChesterfield 0-0 Coventry City | Sky Bet League Two |
| 7 | Sat 9 Sep 2017 | 111-5 v Crewe AlexandraCrewe Alexandra 5-1 Chesterfield | Sky Bet League Two |
| 8 | Tue 12 Sep 2017 | 111-1 v Colchester UnitedColchester United 1-1 Chesterfield | Sky Bet League Two |
| 9 | Sat 16 Sep 2017 | 111-2 v Accrington StanleyChesterfield 1-2 Accrington Stanley | Sky Bet League Two |
| 10 | Sat 23 Sep 2017 | 110-1 v Luton TownLuton Town 1-0 Chesterfield | Sky Bet League Two |
| 11 | Tue 26 Sep 2017 | 112-3 v Yeovil TownChesterfield 2-3 Yeovil Town | Sky Bet League Two |
| 12 | Sat 30 Sep 2017 | 110-2 v Cheltenham TownChesterfield 0-2 Cheltenham Town | Sky Bet League Two |
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