| 1 | Sat 25 Aug 2018 | 160-1 v BarnetChesterfield 0-1 Barnet |
| 2 | Mon 27 Aug 2018 | 160-1 v Hartlepool UnitedHartlepool United 1-0 Chesterfield |
| 3 | Sat 1 Sep 2018 | 160-1 v Leyton OrientChesterfield 0-1 Leyton Orient |
| 4 | Sat 8 Sep 2018 | 160-0 v Dover AthleticChesterfield 0-0 Dover Athletic |
| 5 | Sat 29 Sep 2018 | 161-1 v Maidstone UnitedMaidstone United 1-1 Chesterfield |
| 6 | Sat 6 Oct 2018 | 160-0 v AFC FyldeChesterfield 0-0 AFC Fylde |
| 7 | Sat 13 Oct 2018 | 161-1 v FC Halifax TownFC Halifax Town 1-1 Chesterfield |
| 8 | Sat 27 Oct 2018 | 16 1-1 v WrexhamChesterfield 1-1 Wrexham |
| 9 | Tue 30 Oct 2018 | 16 1-1 v Sutton UnitedSutton United 1-1 Chesterfield |
| 10 | Sat 3 Nov 2018 | 16 1-1 v Harrogate TownHarrogate Town 1-1 Chesterfield |
| 11 | Sat 17 Nov 2018 | 16 0-0 v Havant & WaterloovilleChesterfield 0-0 Havant & Waterlooville |
| 12 | Sat 24 Nov 2018 | 161-1 v EastleighEastleigh 1-1 Chesterfield |
| 13 | Tue 27 Nov 2018 | 16 1-1 v BromleyChesterfield 1-1 Bromley |
| 14 | Wed 26 Dec 2018 | 160-4 v Solihull MoorsChesterfield 0-4 Solihull Moors |
| 15 | Sat 29 Dec 2018 | 161-1 v Hartlepool UnitedChesterfield 1-1 Hartlepool United |
| 16 | Sat 26 Jan 2019 | 160-0 v BarrowChesterfield 0-0 Barrow |
| 17 | Tue 12 Mar 2019 | 163-3 v BromleyBromley 3-3 Chesterfield |
| 18 | Sat 16 Mar 2019 | 162-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Chesterfield |
| 19 | Sat 23 Mar 2019 | 163-0 v Sutton UnitedChesterfield 3-0 Sutton United |
| 20 | Sat 30 Mar 2019 | 162-0 v Dagenham & RedbridgeChesterfield 2-0 Dagenham & Redbridge |
| 21 | Sat 13 Apr 2019 | 164-1 v Maidstone UnitedChesterfield 4-1 Maidstone United |
| 22 | Mon 22 Apr 2019 | 163-2 v Boreham WoodChesterfield 3-2 Boreham Wood |
| 23 | Sat 27 Apr 2019 | 160-2 v Maidenhead UnitedMaidenhead United 2-0 Chesterfield |
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