| 1 | 28/7/2018 | 60-2 v Alfreton TownAlfreton Town 2-0 Chesterfield | Friendly |
| 2 | 7/8/2018 | 63-0 v Aldershot TownChesterfield 3-0 Aldershot Town | National League |
| 3 | 14/8/2018 | 62-3 v BarrowBarrow 3-2 Chesterfield | National League |
| 4 | 25/8/2018 | 60-1 v BarnetChesterfield 0-1 Barnet | National League |
| 5 | 1/9/2018 | 60-1 v Leyton OrientChesterfield 0-1 Leyton Orient | National League |
| 6 | 4/9/2018 | 60-1 v Boreham WoodBoreham Wood 1-0 Chesterfield | National League |
| 7 | 8/9/2018 | 60-0 v Dover AthleticChesterfield 0-0 Dover Athletic | National League |
| 8 | 15/9/2018 | 61-1 v Dagenham & RedbridgeDagenham & Redbridge 1-1 Chesterfield | National League |
| 9 | 25/9/2018 | 61-3 v Maidenhead UnitedChesterfield 1-3 Maidenhead United | National League |
| 10 | 29/9/2018 | 61-1 v Maidstone UnitedMaidstone United 1-1 Chesterfield | National League |
| 11 | 6/10/2018 | 60-0 v AFC FyldeChesterfield 0-0 AFC Fylde | National League |
| 12 | 13/10/2018 | 61-1 v FC Halifax TownFC Halifax Town 1-1 Chesterfield | National League |
| 13 | 27/10/2018 | 61-1 v WrexhamChesterfield 1-1 Wrexham | National League |
| 14 | 30/10/2018 | 61-1 v Sutton UnitedSutton United 1-1 Chesterfield | National League |
| 15 | 3/11/2018 | 61-1 v Harrogate TownHarrogate Town 1-1 Chesterfield | National League |
| 16 | 10/11/2018 | 61-1 v Billericay TownChesterfield 1-1 Billericay Town | Emirates FA Cup First Round |
| 17 | 17/11/2018 | 60-0 v Havant & WaterloovilleChesterfield 0-0 Havant & Waterlooville | National League |
| 18 | 20/11/2018 | 6 3-1 v Billericay TownBillericay Town 1-3 Chesterfield | Emirates FA Cup First Round Replay |
| 19 | 24/11/2018 | 61-1 v EastleighEastleigh 1-1 Chesterfield | National League |
| 20 | 27/11/2018 | 61-1 v BromleyChesterfield 1-1 Bromley | National League |
| 21 | 23/2/2019 | 60-1 v Harrogate TownChesterfield 0-1 Harrogate Town | National League |
| 22 | 5/3/2019 | 63-1 v Braintree TownBraintree Town 1-3 Chesterfield | National League |
| 23 | 23/3/2019 | 63-0 v Sutton UnitedChesterfield 3-0 Sutton United | National League |
| 24 | 30/3/2019 | 62-0 v Dagenham & RedbridgeChesterfield 2-0 Dagenham & Redbridge | National League |
| 25 | 6/4/2019 | 60-0 v Dover AthleticDover Athletic 0-0 Chesterfield | National League |
| 26 | 13/4/2019 | 64-1 v Maidstone UnitedChesterfield 4-1 Maidstone United | National League |
| 27 | 19/4/2019 | 60-1 v GatesheadGateshead 1-0 Chesterfield | National League |
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