| 1 | 4/8/2018 | 21-0 v Ebbsfleet UnitedEbbsfleet United 0-1 Chesterfield | National League |
| 2 | 11/8/2018 | 21-0 v Braintree TownChesterfield 1-0 Braintree Town | National League |
| 3 | 25/8/2018 | 20-1 v BarnetChesterfield 0-1 Barnet | National League |
| 4 | 4/9/2018 | 20-1 v Boreham WoodBoreham Wood 1-0 Chesterfield | National League |
| 5 | 8/9/2018 | 2 0-0 v Dover AthleticChesterfield 0-0 Dover Athletic | National League |
| 6 | 15/9/2018 | 21-1 v Dagenham & RedbridgeDagenham & Redbridge 1-1 Chesterfield | National League |
| 7 | 24/11/2018 | 1-1 v EastleighEastleigh 1-1 Chesterfield | National League |
| 8 | 27/11/2018 | 21-1 v BromleyChesterfield 1-1 Bromley | National League |
| 9 | 2/12/2018 | 20-2 v Grimsby TownChesterfield 0-2 Grimsby Town | Emirates FA Cup Second Round |
| 10 | 8/12/2018 | 2 2-0 v Salford CityChesterfield 2-0 Salford City | National League |
| 11 | 29/12/2018 | 21-1 v Hartlepool UnitedChesterfield 1-1 Hartlepool United | National League |
| 12 | 1/1/2019 | 22-2 v Solihull MoorsSolihull Moors 2-2 Chesterfield | National League |
| 13 | 5/1/2019 | 23-3 v Ebbsfleet UnitedChesterfield 3-3 Ebbsfleet United | National League |
| 14 | 19/1/2019 | 2 2-0 v Aldershot TownAldershot Town 0-2 Chesterfield | National League |
| 15 | 26/1/2019 | 20-0 v BarrowChesterfield 0-0 Barrow | National League |
| 16 | 16/3/2019 | 22-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Chesterfield | National League |
| 17 | 6/4/2019 | 20-0 v Dover AthleticDover Athletic 0-0 Chesterfield | National League |
| 18 | 13/4/2019 | 24-1 v Maidstone UnitedChesterfield 4-1 Maidstone United | National League |
| 19 | 19/4/2019 | 20-1 v GatesheadGateshead 1-0 Chesterfield | National League |
| 20 | 22/4/2019 | 23-2 v Boreham WoodChesterfield 3-2 Boreham Wood | National League |
| 21 | 27/4/2019 | 20-2 v Maidenhead UnitedMaidenhead United 2-0 Chesterfield | National League |
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