| 1 | 7/8/2018 | 323-0 v Aldershot TownChesterfield 3-0 Aldershot Town | National League |
| 2 | 11/8/2018 | 321-0 v Braintree TownChesterfield 1-0 Braintree Town | National League |
| 3 | 14/8/2018 | 322-3 v BarrowBarrow 3-2 Chesterfield | National League |
| 4 | 25/8/2018 | 320-1 v BarnetChesterfield 0-1 Barnet | National League |
| 5 | 27/8/2018 | 320-1 v Hartlepool UnitedHartlepool United 1-0 Chesterfield | National League |
| 6 | 4/9/2018 | 320-1 v Boreham WoodBoreham Wood 1-0 Chesterfield | National League |
| 7 | 25/9/2018 | 321-3 v Maidenhead UnitedChesterfield 1-3 Maidenhead United | National League |
| 8 | 29/9/2018 | 321-1 v Maidstone UnitedMaidstone United 1-1 Chesterfield | National League |
| 9 | 6/10/2018 | 320-0 v AFC FyldeChesterfield 0-0 AFC Fylde | National League |
| 10 | 13/10/2018 | 321-1 v FC Halifax TownFC Halifax Town 1-1 Chesterfield | National League |
| 11 | 10/11/2018 | 321-1 v Billericay TownChesterfield 1-1 Billericay Town | Emirates FA Cup First Round |
| 12 | 17/11/2018 | 320-0 v Havant & WaterloovilleChesterfield 0-0 Havant & Waterlooville | National League |
| 13 | 1/1/2019 | 322-2 v Solihull MoorsSolihull Moors 2-2 Chesterfield | National League |
| 14 | 5/1/2019 | 323-3 v Ebbsfleet UnitedChesterfield 3-3 Ebbsfleet United | National League |
| 15 | 19/1/2019 | 322-0 v Aldershot TownAldershot Town 0-2 Chesterfield | National League |
| 16 | 26/1/2019 | 320-0 v BarrowChesterfield 0-0 Barrow | National League |
| 17 | 9/2/2019 | 321-0 v FC Halifax TownChesterfield 1-0 FC Halifax Town | National League |
| 18 | 16/2/2019 | 321-0 v AFC FyldeAFC Fylde 0-1 Chesterfield | National League |
| 19 | 23/2/2019 | 320-1 v Harrogate TownChesterfield 0-1 Harrogate Town | National League |
| 20 | 2/3/2019 | 320-1 v WrexhamWrexham 1-0 Chesterfield | National League |
| 21 | 12/3/2019 | 323-3 v BromleyBromley 3-3 Chesterfield | National League |
| 22 | 23/3/2019 | 323-0 v Sutton UnitedChesterfield 3-0 Sutton United | National League |
| 23 | 6/4/2019 | 320-0 v Dover AthleticDover Athletic 0-0 Chesterfield | National League |
| 24 | 19/4/2019 | 320-1 v GatesheadGateshead 1-0 Chesterfield | National League |
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