| 1 | Sat 4 Aug 2018 | 11-0 v Ebbsfleet UnitedEbbsfleet United 0-1 Chesterfield | National League |
| 2 | Tue 7 Aug 2018 | 13-0 v Aldershot TownChesterfield 3-0 Aldershot Town | National League |
| 3 | Sat 11 Aug 2018 | 11-0 v Braintree TownChesterfield 1-0 Braintree Town | National League |
| 4 | Tue 14 Aug 2018 | 12-3 v BarrowBarrow 3-2 Chesterfield | National League |
| 5 | Sat 8 Sep 2018 | 10-0 v Dover AthleticChesterfield 0-0 Dover Athletic | National League |
| 6 | Sat 15 Sep 2018 | 11-1 v Dagenham & RedbridgeDagenham & Redbridge 1-1 Chesterfield | National League |
| 7 | Sat 22 Sep 2018 | 10-3 v GatesheadChesterfield 0-3 Gateshead | National League |
| 8 | Tue 25 Sep 2018 | 11-3 v Maidenhead UnitedChesterfield 1-3 Maidenhead United | National League |
| 9 | Sat 19 Jan 2019 | 12-0 v Aldershot TownAldershot Town 0-2 Chesterfield | National League |
| 10 | Sat 26 Jan 2019 | 10-0 v BarrowChesterfield 0-0 Barrow | National League |
| 11 | Sat 9 Feb 2019 | 11-0 v FC Halifax TownChesterfield 1-0 FC Halifax Town | National League |
| 12 | Sat 16 Feb 2019 | 11-0 v AFC FyldeAFC Fylde 0-1 Chesterfield | National League |
| 13 | Sat 23 Feb 2019 | 10-1 v Harrogate TownChesterfield 0-1 Harrogate Town | National League |
| 14 | Tue 26 Feb 2019 | 12-0 v BarnetBarnet 0-2 Chesterfield | National League |
| 15 | Sat 2 Mar 2019 | 1 0-1 v WrexhamWrexham 1-0 Chesterfield | National League |
| 16 | Tue 5 Mar 2019 | 13-1 v Braintree TownBraintree Town 1-3 Chesterfield | National League |
| 17 | Sat 9 Mar 2019 | 12-3 v EastleighChesterfield 2-3 Eastleigh | National League |
| 18 | Tue 12 Mar 2019 | 13-3 v BromleyBromley 3-3 Chesterfield | National League |
| 19 | Sat 16 Mar 2019 | 12-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Chesterfield | National League |
| 20 | Sat 23 Mar 2019 | 13-0 v Sutton UnitedChesterfield 3-0 Sutton United | National League |
| 21 | Sat 30 Mar 2019 | 12-0 v Dagenham & RedbridgeChesterfield 2-0 Dagenham & Redbridge | National League |
| 22 | Fri 19 Apr 2019 | 10-1 v GatesheadGateshead 1-0 Chesterfield | National League |
| 23 | Mon 22 Apr 2019 | 13-2 v Boreham WoodChesterfield 3-2 Boreham Wood | National League |
| 24 | Sat 27 Apr 2019 | 10-2 v Maidenhead UnitedMaidenhead United 2-0 Chesterfield | National League |
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