| 1 | Sat 6 Jan 2018 | 0-4 v Accrington StanleyAccrington Stanley 4-0 Chesterfield | Sky Bet League Two |
| 2 | Sat 13 Jan 2018 | 12-0 v Luton TownChesterfield 2-0 Luton Town | Sky Bet League Two |
| 3 | Sat 20 Jan 2018 | 12-1 v Yeovil TownYeovil Town 1-2 Chesterfield | Sky Bet League Two |
| 4 | Sat 27 Jan 2018 | 10-1 v StevenageChesterfield 0-1 Stevenage | Sky Bet League Two |
| 5 | Sat 3 Feb 2018 | 11-2 v Crawley TownChesterfield 1-2 Crawley Town | Sky Bet League Two |
| 6 | Tue 13 Feb 2018 | 12-3 v Cambridge UnitedChesterfield 2-3 Cambridge United | Sky Bet League Two |
| 7 | Sat 17 Feb 2018 | 10-2 v Carlisle UnitedCarlisle United 2-0 Chesterfield | Sky Bet League Two |
| 8 | Sat 24 Feb 2018 | 12-1 v Swindon TownChesterfield 2-1 Swindon Town | Sky Bet League Two |
| 9 | Sat 10 Mar 2018 | 11-3 v Lincoln CityChesterfield 1-3 Lincoln City | Sky Bet League Two |
| 10 | Sat 17 Mar 2018 | 11-1 v Cheltenham TownCheltenham Town 1-1 Chesterfield | Sky Bet League Two |
| 11 | Sun 25 Mar 2018 | 13-1 v Notts CountyChesterfield 3-1 Notts County | Sky Bet League Two |
| 12 | Fri 30 Mar 2018 | 11-2 v Port ValePort Vale 2-1 Chesterfield | Sky Bet League Two |
| 13 | Sat 7 Apr 2018 | 10-1 v Grimsby TownGrimsby Town 1-0 Chesterfield | Sky Bet League Two |
| 14 | Tue 10 Apr 2018 | 12-2 v MorecambeMorecambe 2-2 Chesterfield | Sky Bet League Two |
| 15 | Sat 14 Apr 2018 | 10-1 v Mansfield TownChesterfield 0-1 Mansfield Town | Sky Bet League Two |
| 16 | Tue 17 Apr 2018 | 11-2 v Exeter CityExeter City 2-1 Chesterfield | Sky Bet League Two |
| 17 | Sat 21 Apr 2018 | 11-4 v Forest Green RoversForest Green Rovers 4-1 Chesterfield | Sky Bet League Two |
| 18 | Sat 28 Apr 2018 | 11-2 v Wycombe WanderersChesterfield 1-2 Wycombe Wanderers | Sky Bet League Two |
| 19 | Tue 1 May 2018 | 11-0 v Newport CountyChesterfield 1-0 Newport County | Sky Bet League Two |
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