| 1 | Sat 5 Aug 2017 | 51-3 v Grimsby TownChesterfield 1-3 Grimsby Town | Sky Bet League Two |
| 2 | Tue 8 Aug 2017 | 51-4 v Sheffield WednesdaySheffield Wednesday 4-1 Chesterfield | Carabao Cup First Round |
| 3 | Sat 12 Aug 2017 | 5 0-2 v Notts CountyNotts County 2-0 Chesterfield | Sky Bet League Two |
| 4 | Sat 19 Aug 2017 | 5 2-0 v Port ValeChesterfield 2-0 Port Vale | Sky Bet League Two |
| 5 | Sat 26 Aug 2017 | 51-4 v Newport CountyNewport County 4-1 Chesterfield | Sky Bet League Two |
| 6 | Tue 29 Aug 2017 | 5 2-4 v Bradford CityChesterfield 2-4 Bradford City | Checkatrade Trophy Northern Group F |
| 7 | Sat 2 Sep 2017 | 50-0 v Coventry CityChesterfield 0-0 Coventry City | Sky Bet League Two |
| 8 | Sat 9 Sep 2017 | 51-5 v Crewe AlexandraCrewe Alexandra 5-1 Chesterfield | Sky Bet League Two |
| 9 | Tue 12 Sep 2017 | 51-1 v Colchester UnitedColchester United 1-1 Chesterfield | Sky Bet League Two |
| 10 | Sat 16 Sep 2017 | 51-2 v Accrington StanleyChesterfield 1-2 Accrington Stanley | Sky Bet League Two |
| 11 | Sat 23 Sep 2017 | 50-1 v Luton TownLuton Town 1-0 Chesterfield | Sky Bet League Two |
| 12 | Tue 26 Sep 2017 | 52-3 v Yeovil TownChesterfield 2-3 Yeovil Town | Sky Bet League Two |
| 13 | Sat 30 Sep 2017 | 50-2 v Cheltenham TownChesterfield 0-2 Cheltenham Town | Sky Bet League Two |
| 14 | Tue 3 Oct 2017 | 52-1 v Rotherham UnitedRotherham United 1-2 Chesterfield | Checkatrade Trophy Northern Group F |
| 15 | Sat 7 Oct 2017 | 51-2 v Lincoln CityLincoln City 2-1 Chesterfield | Sky Bet League Two |
| 16 | Sat 14 Oct 2017 | 50-2 v MorecambeChesterfield 0-2 Morecambe | Sky Bet League Two |
| 17 | Tue 17 Oct 2017 | 52-0 v Crawley TownCrawley Town 0-2 Chesterfield | Sky Bet League Two |
| 18 | Sat 21 Oct 2017 | 51-2 v Cambridge UnitedCambridge United 2-1 Chesterfield | Sky Bet League Two |
| 19 | Sat 28 Oct 2017 | 52-2 v Carlisle UnitedChesterfield 2-2 Carlisle United | Sky Bet League Two |
| 20 | Sat 4 Nov 2017 | 50-2 v Bradford CityBradford City 2-0 Chesterfield | Emirates FA Cup First Round |
| 21 | Sat 11 Nov 2017 | 52-2 v Swindon TownSwindon Town 2-2 Chesterfield | Sky Bet League Two |
| 22 | Sat 18 Nov 2017 | 5 1-0 v Exeter CityChesterfield 1-0 Exeter City | Sky Bet League Two |
| 23 | Tue 5 Dec 2017 | 50-2 v Fleetwood TownFleetwood Town 2-0 Chesterfield | Checkatrade Trophy Second Round |
| 24 | Sat 9 Dec 2017 | 52-1 v BarnetChesterfield 2-1 Barnet | Sky Bet League Two |
| 25 | Sat 16 Dec 2017 | 50-1 v Wycombe WanderersWycombe Wanderers 1-0 Chesterfield | Sky Bet League Two |
| 26 | Sat 23 Dec 2017 | 51-5 v StevenageStevenage 5-1 Chesterfield | Sky Bet League Two |
| 27 | Tue 26 Dec 2017 | 50-2 v Crewe AlexandraChesterfield 0-2 Crewe Alexandra | Sky Bet League Two |
| 28 | Sat 30 Dec 2017 | 50-0 v Colchester UnitedChesterfield 0-0 Colchester United | Sky Bet League Two |
| 29 | Mon 1 Jan 2018 | 5 0-1 v Coventry CityCoventry City 1-0 Chesterfield | Sky Bet League Two |
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