| 1 | 15/9/2018 | 1-1 v Dagenham & RedbridgeDagenham & Redbridge 1-1 Chesterfield | National League |
| 2 | 22/9/2018 | 300-3 v GatesheadChesterfield 0-3 Gateshead | National League |
| 3 | 25/9/2018 | 301-3 v Maidenhead UnitedChesterfield 1-3 Maidenhead United | National League |
| 4 | 29/9/2018 | 30 1-1 v Maidstone UnitedMaidstone United 1-1 Chesterfield | National League |
| 5 | 6/10/2018 | 300-0 v AFC FyldeChesterfield 0-0 AFC Fylde | National League |
| 6 | 13/10/2018 | 30 1-1 v FC Halifax TownFC Halifax Town 1-1 Chesterfield | National League |
| 7 | 27/10/2018 | 30 1-1 v WrexhamChesterfield 1-1 Wrexham | National League |
| 8 | 30/10/2018 | 301-1 v Sutton UnitedSutton United 1-1 Chesterfield | National League |
| 9 | 3/11/2018 | 301-1 v Harrogate TownHarrogate Town 1-1 Chesterfield | National League |
| 10 | 10/11/2018 | 301-1 v Billericay TownChesterfield 1-1 Billericay Town | Emirates FA Cup First Round |
| 11 | 20/11/2018 | 303-1 v Billericay TownBillericay Town 1-3 Chesterfield | Emirates FA Cup First Round Replay |
| 12 | 24/11/2018 | 301-1 v EastleighEastleigh 1-1 Chesterfield | National League |
| 13 | 27/11/2018 | 301-1 v BromleyChesterfield 1-1 Bromley | National League |
| 14 | 2/12/2018 | 300-2 v Grimsby TownChesterfield 0-2 Grimsby Town | Emirates FA Cup Second Round |
| 15 | 8/12/2018 | 302-0 v Salford CityChesterfield 2-0 Salford City | National League |
| 16 | 22/12/2018 | 301-3 v Leyton OrientLeyton Orient 3-1 Chesterfield | National League |
| 17 | 5/1/2019 | 303-3 v Ebbsfleet UnitedChesterfield 3-3 Ebbsfleet United | National League |
| 18 | 26/1/2019 | 300-0 v BarrowChesterfield 0-0 Barrow | National League |
| 19 | 9/2/2019 | 301-0 v FC Halifax TownChesterfield 1-0 FC Halifax Town | National League |
| 20 | 23/2/2019 | 300-1 v Harrogate TownChesterfield 0-1 Harrogate Town | National League |
| 21 | 26/2/2019 | 30 2-0 v BarnetBarnet 0-2 Chesterfield | National League |
| 22 | 5/3/2019 | 303-1 v Braintree TownBraintree Town 1-3 Chesterfield | National League |
| 23 | 9/3/2019 | 302-3 v EastleighChesterfield 2-3 Eastleigh | National League |
| 24 | 16/3/2019 | 302-1 v Havant & WaterloovilleHavant & Waterlooville 1-2 Chesterfield | National League |
| 25 | 23/3/2019 | 303-0 v Sutton UnitedChesterfield 3-0 Sutton United | National League |
| 26 | 30/3/2019 | 302-0 v Dagenham & RedbridgeChesterfield 2-0 Dagenham & Redbridge | National League |
| 27 | 6/4/2019 | 300-0 v Dover AthleticDover Athletic 0-0 Chesterfield | National League |
| 28 | 13/4/2019 | 304-1 v Maidstone UnitedChesterfield 4-1 Maidstone United | National League |
| 29 | 19/4/2019 | 300-1 v GatesheadGateshead 1-0 Chesterfield | National League |
| 30 | 22/4/2019 | 30 3-2 v Boreham WoodChesterfield 3-2 Boreham Wood | National League |
| 31 | 27/4/2019 | 300-2 v Maidenhead UnitedMaidenhead United 2-0 Chesterfield | National League |
Football Web Pages