| 1 | 3/8/2019 | 81-2 v Dover AthleticChesterfield 1-2 Dover Athletic | Vanarama National League |
| 2 | 6/8/2019 | 81-1 v Maidenhead UnitedMaidenhead United 1-1 Chesterfield | Vanarama National League |
| 3 | 10/8/2019 | 82-2 v Boreham WoodBoreham Wood 2-2 Chesterfield | Vanarama National League |
| 4 | 13/8/2019 | 81-2 v WokingChesterfield 1-2 Woking | Vanarama National League |
| 5 | 17/8/2019 | 82-2 v BarnetBarnet 2-2 Chesterfield | Vanarama National League |
| 6 | 31/8/2019 | 81-1 v Dagenham & RedbridgeChesterfield 1-1 Dagenham & Redbridge | Vanarama National League |
| 7 | 3/9/2019 | 82-3 v FC Halifax TownChesterfield 2-3 FC Halifax Town | Vanarama National League |
| 8 | 7/9/2019 | 81-2 v BromleyBromley 2-1 Chesterfield | Vanarama National League |
| 9 | 14/9/2019 | 81-0 v Torquay UnitedChesterfield 1-0 Torquay United | Vanarama National League |
| 10 | 21/9/2019 | 80-4 v Sutton UnitedSutton United 4-0 Chesterfield | Vanarama National League |
| 11 | 24/9/2019 | 81-1 v Hartlepool UnitedHartlepool United 1-1 Chesterfield | Vanarama National League |
| 12 | 28/9/2019 | 82-1 v Aldershot TownChesterfield 2-1 Aldershot Town | Vanarama National League |
| 13 | 5/10/2019 | 81-2 v EastleighChesterfield 1-2 Eastleigh | Vanarama National League |
| 14 | 8/10/2019 | 83-1 v AFC FyldeAFC Fylde 1-3 Chesterfield | Vanarama National League |
| 15 | 26/10/2019 | 81-0 v Notts CountyChesterfield 1-0 Notts County | Vanarama National League |
| 16 | 16/11/2019 | 82-3 v ChorleyChesterfield 2-3 Chorley | Vanarama National League |
| 17 | 23/11/2019 | 81-3 v Harrogate TownHarrogate Town 3-1 Chesterfield | Vanarama National League |
| 18 | 30/11/2019 | 82-2 v Aldershot TownAldershot Town 2-2 Chesterfield | Vanarama National League |
| 19 | 7/12/2019 | 81-2 v BromleyChesterfield 1-2 Bromley | Vanarama National League |
| 20 | 10/12/2019 | 81-2 v Yeovil TownChesterfield 1-2 Yeovil Town | Vanarama National League |
