| 1 | Sat 5 Aug 2017 | 101-3 v Grimsby TownChesterfield 1-3 Grimsby Town | Sky Bet League Two |
| 2 | Tue 8 Aug 2017 | 10 1-4 v Sheffield WednesdaySheffield Wednesday 4-1 Chesterfield | Carabao Cup First Round |
| 3 | Sat 12 Aug 2017 | 100-2 v Notts CountyNotts County 2-0 Chesterfield | Sky Bet League Two |
| 4 | Sat 19 Aug 2017 | 102-0 v Port ValeChesterfield 2-0 Port Vale | Sky Bet League Two |
| 5 | Sat 26 Aug 2017 | 101-4 v Newport CountyNewport County 4-1 Chesterfield | Sky Bet League Two |
| 6 | Tue 29 Aug 2017 | 102-4 v Bradford CityChesterfield 2-4 Bradford City | Checkatrade Trophy Northern Group F |
| 7 | Sat 2 Sep 2017 | 100-0 v Coventry CityChesterfield 0-0 Coventry City | Sky Bet League Two |
| 8 | Sat 9 Sep 2017 | 101-5 v Crewe AlexandraCrewe Alexandra 5-1 Chesterfield | Sky Bet League Two |
| 9 | Tue 12 Sep 2017 | 101-1 v Colchester UnitedColchester United 1-1 Chesterfield | Sky Bet League Two |
| 10 | Sat 23 Sep 2017 | 100-1 v Luton TownLuton Town 1-0 Chesterfield | Sky Bet League Two |
| 11 | Tue 26 Sep 2017 | 102-3 v Yeovil TownChesterfield 2-3 Yeovil Town | Sky Bet League Two |
| 12 | Sat 30 Sep 2017 | 10 0-2 v Cheltenham TownChesterfield 0-2 Cheltenham Town | Sky Bet League Two |
| 13 | Tue 3 Oct 2017 | 102-1 v Rotherham UnitedRotherham United 1-2 Chesterfield | Checkatrade Trophy Northern Group F |
| 14 | Sat 7 Oct 2017 | 101-2 v Lincoln CityLincoln City 2-1 Chesterfield | Sky Bet League Two |
| 15 | Sat 14 Oct 2017 | 100-2 v MorecambeChesterfield 0-2 Morecambe | Sky Bet League Two |
| 16 | Sat 28 Oct 2017 | 102-2 v Carlisle UnitedChesterfield 2-2 Carlisle United | Sky Bet League Two |
| 17 | Sat 18 Nov 2017 | 101-0 v Exeter CityChesterfield 1-0 Exeter City | Sky Bet League Two |
| 18 | Tue 21 Nov 2017 | 103-2 v Forest Green RoversChesterfield 3-2 Forest Green Rovers | Sky Bet League Two |
| 19 | Tue 5 Dec 2017 | 100-2 v Fleetwood TownFleetwood Town 2-0 Chesterfield | Checkatrade Trophy Second Round |
| 20 | Sat 9 Dec 2017 | 102-1 v BarnetChesterfield 2-1 Barnet | Sky Bet League Two |
| 21 | Sat 16 Dec 2017 | 100-1 v Wycombe WanderersWycombe Wanderers 1-0 Chesterfield | Sky Bet League Two |
| 22 | Sat 23 Dec 2017 | 101-5 v StevenageStevenage 5-1 Chesterfield | Sky Bet League Two |
| 23 | Tue 26 Dec 2017 | 100-2 v Crewe AlexandraChesterfield 0-2 Crewe Alexandra | Sky Bet League Two |
| 24 | Mon 1 Jan 2018 | 100-1 v Coventry CityCoventry City 1-0 Chesterfield | Sky Bet League Two |
| 25 | Sat 13 Jan 2018 | 102-0 v Luton TownChesterfield 2-0 Luton Town | Sky Bet League Two |
| 26 | Sat 20 Jan 2018 | 102-1 v Yeovil TownYeovil Town 1-2 Chesterfield | Sky Bet League Two |
| 27 | Sat 27 Jan 2018 | 100-1 v StevenageChesterfield 0-1 Stevenage | Sky Bet League Two |
| 28 | Sat 3 Feb 2018 | 101-2 v Crawley TownChesterfield 1-2 Crawley Town | Sky Bet League Two |
| 29 | Tue 13 Feb 2018 | 10 2-3 v Cambridge UnitedChesterfield 2-3 Cambridge United | Sky Bet League Two |
| 30 | Sat 17 Feb 2018 | 100-2 v Carlisle UnitedCarlisle United 2-0 Chesterfield | Sky Bet League Two |
| 31 | Sat 24 Feb 2018 | 102-1 v Swindon TownChesterfield 2-1 Swindon Town | Sky Bet League Two |
| 32 | Sat 10 Mar 2018 | 101-3 v Lincoln CityChesterfield 1-3 Lincoln City | Sky Bet League Two |
| 33 | Sat 7 Apr 2018 | 100-1 v Grimsby TownGrimsby Town 1-0 Chesterfield | Sky Bet League Two |
| 34 | Tue 10 Apr 2018 | 102-2 v MorecambeMorecambe 2-2 Chesterfield | Sky Bet League Two |
| 35 | Sat 14 Apr 2018 | 100-1 v Mansfield TownChesterfield 0-1 Mansfield Town | Sky Bet League Two |
| 36 | Tue 17 Apr 2018 | 101-2 v Exeter CityExeter City 2-1 Chesterfield | Sky Bet League Two |
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