| 1 | 4/8/2018 | 51-0 v Ebbsfleet UnitedEbbsfleet United 0-1 Chesterfield | National League |
| 2 | 7/8/2018 | 53-0 v Aldershot TownChesterfield 3-0 Aldershot Town | National League |
| 3 | 11/8/2018 | 51-0 v Braintree TownChesterfield 1-0 Braintree Town | National League |
| 4 | 14/8/2018 | 5 2-3 v BarrowBarrow 3-2 Chesterfield | National League |
| 5 | 25/8/2018 | 50-1 v BarnetChesterfield 0-1 Barnet | National League |
| 6 | 27/8/2018 | 50-1 v Hartlepool UnitedHartlepool United 1-0 Chesterfield | National League |
| 7 | 1/9/2018 | 5 0-1 v Leyton OrientChesterfield 0-1 Leyton Orient | National League |
| 8 | 8/9/2018 | 50-0 v Dover AthleticChesterfield 0-0 Dover Athletic | National League |
| 9 | 15/9/2018 | 51-1 v Dagenham & RedbridgeDagenham & Redbridge 1-1 Chesterfield | National League |
| 10 | 29/9/2018 | 51-1 v Maidstone UnitedMaidstone United 1-1 Chesterfield | National League |
| 11 | 6/10/2018 | 50-0 v AFC FyldeChesterfield 0-0 AFC Fylde | National League |
| 12 | 13/10/2018 | 51-1 v FC Halifax TownFC Halifax Town 1-1 Chesterfield | National League |
| 13 | 27/10/2018 | 5 1-1 v WrexhamChesterfield 1-1 Wrexham | National League |
| 14 | 3/11/2018 | 51-1 v Harrogate TownHarrogate Town 1-1 Chesterfield | National League |
| 15 | 10/11/2018 | 51-1 v Billericay TownChesterfield 1-1 Billericay Town | Emirates FA Cup First Round |
| 16 | 17/11/2018 | 50-0 v Havant & WaterloovilleChesterfield 0-0 Havant & Waterlooville | National League |
| 17 | 20/11/2018 | 53-1 v Billericay TownBillericay Town 1-3 Chesterfield | Emirates FA Cup First Round Replay |
| 18 | 2/12/2018 | 50-2 v Grimsby TownChesterfield 0-2 Grimsby Town | Emirates FA Cup Second Round |
| 19 | 8/12/2018 | 52-0 v Salford CityChesterfield 2-0 Salford City | National League |
| 20 | 22/12/2018 | 5 1-3 v Leyton OrientLeyton Orient 3-1 Chesterfield | National League |
| 21 | 26/12/2018 | 50-4 v Solihull MoorsChesterfield 0-4 Solihull Moors | National League |
| 22 | 29/12/2018 | 51-1 v Hartlepool UnitedChesterfield 1-1 Hartlepool United | National League |
| 23 | 1/1/2019 | 52-2 v Solihull MoorsSolihull Moors 2-2 Chesterfield | National League |
| 24 | 5/1/2019 | 53-3 v Ebbsfleet UnitedChesterfield 3-3 Ebbsfleet United | National League |
| 25 | 19/1/2019 | 52-0 v Aldershot TownAldershot Town 0-2 Chesterfield | National League |
| 26 | 26/1/2019 | 50-0 v BarrowChesterfield 0-0 Barrow | National League |
| 27 | 9/2/2019 | 51-0 v FC Halifax TownChesterfield 1-0 FC Halifax Town | National League |
| 28 | 16/2/2019 | 51-0 v AFC FyldeAFC Fylde 0-1 Chesterfield | National League |
| 29 | 26/2/2019 | 52-0 v BarnetBarnet 0-2 Chesterfield | National League |
| 30 | 2/3/2019 | 50-1 v WrexhamWrexham 1-0 Chesterfield | National League |
| 31 | 5/3/2019 | 53-1 v Braintree TownBraintree Town 1-3 Chesterfield | National League |
| 32 | 9/3/2019 | 52-3 v EastleighChesterfield 2-3 Eastleigh | National League |
| 33 | 12/3/2019 | 53-3 v BromleyBromley 3-3 Chesterfield | National League |
| 34 | 16/3/2019 | 52-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Chesterfield | National League |
| 35 | 23/3/2019 | 53-0 v Sutton UnitedChesterfield 3-0 Sutton United | National League |
| 36 | 30/3/2019 | 5 2-0 v Dagenham & RedbridgeChesterfield 2-0 Dagenham & Redbridge | National League |
| 37 | 6/4/2019 | 50-0 v Dover AthleticDover Athletic 0-0 Chesterfield | National League |
| 38 | 13/4/2019 | 54-1 v Maidstone UnitedChesterfield 4-1 Maidstone United | National League |
| 39 | 19/4/2019 | 5 0-1 v GatesheadGateshead 1-0 Chesterfield | National League |
| 40 | 22/4/2019 | 53-2 v Boreham WoodChesterfield 3-2 Boreham Wood | National League |
| 41 | 27/4/2019 | 50-2 v Maidenhead UnitedMaidenhead United 2-0 Chesterfield | National League |
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