| 1 | Sat 21 Sep 2019 | 0-4 v Sutton UnitedSutton United 4-0 Chesterfield | Vanarama National League |
| 2 | Tue 24 Sep 2019 | 1-1 v Hartlepool UnitedHartlepool United 1-1 Chesterfield | Vanarama National League |
| 3 | Sat 28 Sep 2019 | 2-1 v Aldershot TownChesterfield 2-1 Aldershot Town | Vanarama National League |
| 4 | Sat 5 Oct 2019 | 1-2 v EastleighChesterfield 1-2 Eastleigh | Vanarama National League |
| 5 | Sat 26 Oct 2019 | 1-0 v Notts CountyChesterfield 1-0 Notts County | Vanarama National League |
| 6 | Sat 2 Nov 2019 | 2-2 v Ebbsfleet UnitedEbbsfleet United 2-2 Chesterfield | Vanarama National League |
| 7 | Sat 23 Nov 2019 | 1-3 v Harrogate TownHarrogate Town 3-1 Chesterfield | Vanarama National League |
| 8 | Tue 26 Nov 2019 | 1-5 v Hartlepool UnitedChesterfield 1-5 Hartlepool United | Vanarama National League |
| 9 | Sat 30 Nov 2019 | 2-2 v Aldershot TownAldershot Town 2-2 Chesterfield | Vanarama National League |
| 10 | Sat 7 Dec 2019 | 1-2 v BromleyChesterfield 1-2 Bromley | Vanarama National League |
| 11 | Tue 10 Dec 2019 | 1-2 v Yeovil TownChesterfield 1-2 Yeovil Town | Vanarama National League |
| 12 | Sat 14 Dec 2019 | 0-1 v Notts CountyChesterfield 0-1 Notts County | Buildbase FA Trophy First Round |
| 13 | Sat 21 Dec 2019 | 3-0 v Torquay UnitedTorquay United 0-3 Chesterfield | Vanarama National League |
| 14 | Thu 26 Dec 2019 | 2-2 v Solihull MoorsChesterfield 2-2 Solihull Moors | Vanarama National League |
| 15 | Sat 28 Dec 2019 | 0-1 v FC Halifax TownFC Halifax Town 1-0 Chesterfield | Vanarama National League |
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