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