| 1 | Tue 7 Aug 2018 | 63-0 v Aldershot TownChesterfield 3-0 Aldershot Town |
| 2 | Tue 14 Aug 2018 | 62-3 v BarrowBarrow 3-2 Chesterfield |
| 3 | Sat 25 Aug 2018 | 60-1 v BarnetChesterfield 0-1 Barnet |
| 4 | Sat 1 Sep 2018 | 60-1 v Leyton OrientChesterfield 0-1 Leyton Orient |
| 5 | Tue 4 Sep 2018 | 60-1 v Boreham WoodBoreham Wood 1-0 Chesterfield |
| 6 | Sat 8 Sep 2018 | 60-0 v Dover AthleticChesterfield 0-0 Dover Athletic |
| 7 | Sat 15 Sep 2018 | 61-1 v Dagenham & RedbridgeDagenham & Redbridge 1-1 Chesterfield |
| 8 | Tue 25 Sep 2018 | 61-3 v Maidenhead UnitedChesterfield 1-3 Maidenhead United |
| 9 | Sat 29 Sep 2018 | 61-1 v Maidstone UnitedMaidstone United 1-1 Chesterfield |
| 10 | Sat 6 Oct 2018 | 60-0 v AFC FyldeChesterfield 0-0 AFC Fylde |
| 11 | Sat 13 Oct 2018 | 61-1 v FC Halifax TownFC Halifax Town 1-1 Chesterfield |
| 12 | Sat 27 Oct 2018 | 61-1 v WrexhamChesterfield 1-1 Wrexham |
| 13 | Tue 30 Oct 2018 | 61-1 v Sutton UnitedSutton United 1-1 Chesterfield |
| 14 | Sat 3 Nov 2018 | 61-1 v Harrogate TownHarrogate Town 1-1 Chesterfield |
| 15 | Sat 17 Nov 2018 | 60-0 v Havant & WaterloovilleChesterfield 0-0 Havant & Waterlooville |
| 16 | Sat 24 Nov 2018 | 61-1 v EastleighEastleigh 1-1 Chesterfield |
| 17 | Tue 27 Nov 2018 | 61-1 v BromleyChesterfield 1-1 Bromley |
| 18 | Sat 23 Feb 2019 | 60-1 v Harrogate TownChesterfield 0-1 Harrogate Town |
| 19 | Tue 5 Mar 2019 | 63-1 v Braintree TownBraintree Town 1-3 Chesterfield |
| 20 | Sat 23 Mar 2019 | 63-0 v Sutton UnitedChesterfield 3-0 Sutton United |
| 21 | Sat 30 Mar 2019 | 62-0 v Dagenham & RedbridgeChesterfield 2-0 Dagenham & Redbridge |
| 22 | Sat 6 Apr 2019 | 60-0 v Dover AthleticDover Athletic 0-0 Chesterfield |
| 23 | Sat 13 Apr 2019 | 64-1 v Maidstone UnitedChesterfield 4-1 Maidstone United |
| 24 | Fri 19 Apr 2019 | 60-1 v GatesheadGateshead 1-0 Chesterfield |
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