| 1 | 17/8/2019 | 2-2 v BarnetBarnet 2-2 Chesterfield | Vanarama National League |
| 2 | 24/8/2019 | 2-2 v BarrowChesterfield 2-2 Barrow | Vanarama National League |
| 3 | 31/8/2019 | 1-1 v Dagenham & RedbridgeChesterfield 1-1 Dagenham & Redbridge | Vanarama National League |
| 4 | 3/9/2019 | 2-3 v FC Halifax TownChesterfield 2-3 FC Halifax Town | Vanarama National League |
| 5 | 7/9/2019 | 1-2 v BromleyBromley 2-1 Chesterfield | Vanarama National League |
| 6 | 26/10/2019 | 1-0 v Notts CountyChesterfield 1-0 Notts County | Vanarama National League |
| 7 | 30/11/2019 | 2-2 v Aldershot TownAldershot Town 2-2 Chesterfield | Vanarama National League |
| 8 | 7/12/2019 | 1-2 v BromleyChesterfield 1-2 Bromley | Vanarama National League |
