| 1 | Sat 25 Aug 2018 | 0-1 v BarnetChesterfield 0-1 Barnet | National League |
| 2 | Mon 27 Aug 2018 | 310-1 v Hartlepool UnitedHartlepool United 1-0 Chesterfield | National League |
| 3 | Sat 1 Sep 2018 | 310-1 v Leyton OrientChesterfield 0-1 Leyton Orient | National League |
| 4 | Tue 4 Sep 2018 | 310-1 v Boreham WoodBoreham Wood 1-0 Chesterfield | National League |
| 5 | Sat 29 Sep 2018 | 311-1 v Maidstone UnitedMaidstone United 1-1 Chesterfield | National League |
| 6 | Sat 6 Oct 2018 | 310-0 v AFC FyldeChesterfield 0-0 AFC Fylde | National League |
| 7 | Sat 13 Oct 2018 | 311-1 v FC Halifax TownFC Halifax Town 1-1 Chesterfield | National League |
| 8 | Sat 27 Oct 2018 | 311-1 v WrexhamChesterfield 1-1 Wrexham | National League |
| 9 | Tue 30 Oct 2018 | 311-1 v Sutton UnitedSutton United 1-1 Chesterfield | National League |
| 10 | Sat 3 Nov 2018 | 311-1 v Harrogate TownHarrogate Town 1-1 Chesterfield | National League |
| 11 | Sat 10 Nov 2018 | 311-1 v Billericay TownChesterfield 1-1 Billericay Town | Emirates FA Cup First Round |
| 12 | Sat 17 Nov 2018 | 310-0 v Havant & WaterloovilleChesterfield 0-0 Havant & Waterlooville | National League |
| 13 | Tue 20 Nov 2018 | 313-1 v Billericay TownBillericay Town 1-3 Chesterfield | Emirates FA Cup First Round Replay |
| 14 | Tue 27 Nov 2018 | 311-1 v BromleyChesterfield 1-1 Bromley | National League |
| 15 | Sun 2 Dec 2018 | 310-2 v Grimsby TownChesterfield 0-2 Grimsby Town | Emirates FA Cup Second Round |
| 16 | Sat 8 Dec 2018 | 312-0 v Salford CityChesterfield 2-0 Salford City | National League |
| 17 | Sat 22 Dec 2018 | 311-3 v Leyton OrientLeyton Orient 3-1 Chesterfield | National League |
| 18 | Wed 26 Dec 2018 | 310-4 v Solihull MoorsChesterfield 0-4 Solihull Moors | National League |
| 19 | Sat 29 Dec 2018 | 311-1 v Hartlepool UnitedChesterfield 1-1 Hartlepool United | National League |
| 20 | Tue 1 Jan 2019 | 312-2 v Solihull MoorsSolihull Moors 2-2 Chesterfield | National League |
| 21 | Sat 5 Jan 2019 | 31 3-3 v Ebbsfleet UnitedChesterfield 3-3 Ebbsfleet United | National League |
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