| 1 | Sat 4 Aug 2018 | 111-0 v Ebbsfleet UnitedEbbsfleet United 0-1 Chesterfield |
| 2 | Tue 7 Aug 2018 | 11 3-0 v Aldershot TownChesterfield 3-0 Aldershot Town |
| 3 | Sat 11 Aug 2018 | 11 1-0 v Braintree TownChesterfield 1-0 Braintree Town |
| 4 | Tue 14 Aug 2018 | 112-3 v BarrowBarrow 3-2 Chesterfield |
| 5 | Sat 25 Aug 2018 | 110-1 v BarnetChesterfield 0-1 Barnet |
| 6 | Mon 27 Aug 2018 | 110-1 v Hartlepool UnitedHartlepool United 1-0 Chesterfield |
| 7 | Sat 1 Sep 2018 | 110-1 v Leyton OrientChesterfield 0-1 Leyton Orient |
| 8 | Tue 4 Sep 2018 | 11 0-1 v Boreham WoodBoreham Wood 1-0 Chesterfield |
| 9 | Sat 8 Sep 2018 | 110-0 v Dover AthleticChesterfield 0-0 Dover Athletic |
| 10 | Sat 15 Sep 2018 | 111-1 v Dagenham & RedbridgeDagenham & Redbridge 1-1 Chesterfield |
| 11 | Sat 13 Oct 2018 | 111-1 v FC Halifax TownFC Halifax Town 1-1 Chesterfield |
| 12 | Sat 27 Oct 2018 | 111-1 v WrexhamChesterfield 1-1 Wrexham |
| 13 | Sat 3 Nov 2018 | 11 1-1 v Harrogate TownHarrogate Town 1-1 Chesterfield |
| 14 | Tue 27 Nov 2018 | 111-1 v BromleyChesterfield 1-1 Bromley |
| 15 | Wed 26 Dec 2018 | 210-1 v Sutton UnitedSutton United 1-0 Bromley |
| 16 | Tue 1 Jan 2019 | 212-1 v Sutton UnitedBromley 2-1 Sutton United |
| 17 | Sat 5 Jan 2019 | 21 3-2 v AFC FyldeBromley 3-2 AFC Fylde |
| 18 | Sat 27 Apr 2019 | 215-1 v Ebbsfleet UnitedBromley 5-1 Ebbsfleet United |
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