| 1 | Sat 24 Aug 2019 | 2-2 v BarrowChesterfield 2-2 Barrow | Vanarama National League |
| 2 | Tue 8 Oct 2019 | 3-1 v AFC FyldeAFC Fylde 1-3 Chesterfield | Vanarama National League |
| 3 | Sat 26 Oct 2019 | 1-0 v Notts CountyChesterfield 1-0 Notts County | Vanarama National League |
| 4 | Sat 2 Nov 2019 | 2-2 v Ebbsfleet UnitedEbbsfleet United 2-2 Chesterfield | Vanarama National League |
| 5 | Sat 16 Nov 2019 | 2-3 v ChorleyChesterfield 2-3 Chorley | Vanarama National League |
| 6 | Sat 23 Nov 2019 | 1-3 v Harrogate TownHarrogate Town 3-1 Chesterfield | Vanarama National League |
| 7 | Tue 26 Nov 2019 | 1-5 v Hartlepool UnitedChesterfield 1-5 Hartlepool United | Vanarama National League |
| 8 | Sat 30 Nov 2019 | 2-2 v Aldershot TownAldershot Town 2-2 Chesterfield | Vanarama National League |
| 9 | Sat 7 Dec 2019 | 1-2 v BromleyChesterfield 1-2 Bromley | Vanarama National League |
| 10 | Tue 10 Dec 2019 | 1-2 v Yeovil TownChesterfield 1-2 Yeovil Town | Vanarama National League |
| 11 | Sat 21 Dec 2019 | 3-0 v Torquay UnitedTorquay United 0-3 Chesterfield | Vanarama National League |
| 12 | Thu 26 Dec 2019 | 2-2 v Solihull MoorsChesterfield 2-2 Solihull Moors | Vanarama National League |
| 13 | Sat 28 Dec 2019 | 0-1 v FC Halifax TownFC Halifax Town 1-0 Chesterfield | Vanarama National League |
| 14 | Wed 1 Jan 2020 | 0-3 v Solihull MoorsSolihull Moors 3-0 Chesterfield | Vanarama National League |
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