| 1 | Sat 28 Jul 2018 | 160-2 v Alfreton TownAlfreton Town 2-0 Chesterfield | Friendly |
| 2 | Sat 25 Aug 2018 | 160-1 v BarnetChesterfield 0-1 Barnet | National League |
| 3 | Mon 27 Aug 2018 | 160-1 v Hartlepool UnitedHartlepool United 1-0 Chesterfield | National League |
| 4 | Sat 1 Sep 2018 | 160-1 v Leyton OrientChesterfield 0-1 Leyton Orient | National League |
| 5 | Sat 8 Sep 2018 | 160-0 v Dover AthleticChesterfield 0-0 Dover Athletic | National League |
| 6 | Sat 29 Sep 2018 | 161-1 v Maidstone UnitedMaidstone United 1-1 Chesterfield | National League |
| 7 | Sat 6 Oct 2018 | 160-0 v AFC FyldeChesterfield 0-0 AFC Fylde | National League |
| 8 | Sat 13 Oct 2018 | 161-1 v FC Halifax TownFC Halifax Town 1-1 Chesterfield | National League |
| 9 | Sat 27 Oct 2018 | 16 1-1 v WrexhamChesterfield 1-1 Wrexham | National League |
| 10 | Tue 30 Oct 2018 | 16 1-1 v Sutton UnitedSutton United 1-1 Chesterfield | National League |
| 11 | Sat 3 Nov 2018 | 16 1-1 v Harrogate TownHarrogate Town 1-1 Chesterfield | National League |
| 12 | Sat 10 Nov 2018 | 161-1 v Billericay TownChesterfield 1-1 Billericay Town | Emirates FA Cup First Round |
| 13 | Sat 17 Nov 2018 | 16 0-0 v Havant & WaterloovilleChesterfield 0-0 Havant & Waterlooville | National League |
| 14 | Tue 20 Nov 2018 | 163-1 v Billericay TownBillericay Town 1-3 Chesterfield | Emirates FA Cup First Round Replay |
| 15 | Sat 24 Nov 2018 | 161-1 v EastleighEastleigh 1-1 Chesterfield | National League |
| 16 | Tue 27 Nov 2018 | 16 1-1 v BromleyChesterfield 1-1 Bromley | National League |
| 17 | Sun 2 Dec 2018 | 160-2 v Grimsby TownChesterfield 0-2 Grimsby Town | Emirates FA Cup Second Round |
| 18 | Wed 26 Dec 2018 | 160-4 v Solihull MoorsChesterfield 0-4 Solihull Moors | National League |
| 19 | Sat 29 Dec 2018 | 161-1 v Hartlepool UnitedChesterfield 1-1 Hartlepool United | National League |
| 20 | Sat 26 Jan 2019 | 160-0 v BarrowChesterfield 0-0 Barrow | National League |
| 21 | Tue 12 Mar 2019 | 163-3 v BromleyBromley 3-3 Chesterfield | National League |
| 22 | Sat 16 Mar 2019 | 162-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Chesterfield | National League |
| 23 | Sat 23 Mar 2019 | 163-0 v Sutton UnitedChesterfield 3-0 Sutton United | National League |
| 24 | Sat 30 Mar 2019 | 162-0 v Dagenham & RedbridgeChesterfield 2-0 Dagenham & Redbridge | National League |
| 25 | Sat 13 Apr 2019 | 164-1 v Maidstone UnitedChesterfield 4-1 Maidstone United | National League |
| 26 | Mon 22 Apr 2019 | 163-2 v Boreham WoodChesterfield 3-2 Boreham Wood | National League |
| 27 | Sat 27 Apr 2019 | 160-2 v Maidenhead UnitedMaidenhead United 2-0 Chesterfield | National League |
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