| 1 | Sat 3 Aug 2019 | 1-2 v Dover AthleticChesterfield 1-2 Dover Athletic | Vanarama National League |
| 2 | Tue 6 Aug 2019 | 1-1 v Maidenhead UnitedMaidenhead United 1-1 Chesterfield | Vanarama National League |
| 3 | Sat 10 Aug 2019 | 2-2 v Boreham WoodBoreham Wood 2-2 Chesterfield | Vanarama National League |
| 4 | Tue 13 Aug 2019 | 1-2 v WokingChesterfield 1-2 Woking | Vanarama National League |
| 5 | Sat 17 Aug 2019 | 2-2 v BarnetBarnet 2-2 Chesterfield | Vanarama National League |
| 6 | Sat 24 Aug 2019 | 2-2 v BarrowChesterfield 2-2 Barrow | Vanarama National League |
| 7 | Sat 2 Nov 2019 | 2-2 v Ebbsfleet UnitedEbbsfleet United 2-2 Chesterfield | Vanarama National League |
| 8 | Sat 16 Nov 2019 | 2-3 v ChorleyChesterfield 2-3 Chorley | Vanarama National League |
| 9 | Sat 23 Nov 2019 | 1-3 v Harrogate TownHarrogate Town 3-1 Chesterfield | Vanarama National League |
| 10 | Sat 30 Nov 2019 | 2-2 v Aldershot TownAldershot Town 2-2 Chesterfield | Vanarama National League |
| 11 | Sat 14 Dec 2019 | 0-1 v Notts CountyChesterfield 0-1 Notts County | Buildbase FA Trophy First Round |
| 12 | Sat 21 Dec 2019 | 3-0 v Torquay UnitedTorquay United 0-3 Chesterfield | Vanarama National League |
| 13 | Thu 26 Dec 2019 | 2-2 v Solihull MoorsChesterfield 2-2 Solihull Moors | Vanarama National League |
| 14 | Sat 28 Dec 2019 | 0-1 v FC Halifax TownFC Halifax Town 1-0 Chesterfield | Vanarama National League |
| 15 | Wed 1 Jan 2020 | 0-3 v Solihull MoorsSolihull Moors 3-0 Chesterfield | Vanarama National League |
| 16 | Sat 4 Jan 2020 | 1-0 v Sutton UnitedChesterfield 1-0 Sutton United | Vanarama National League |
| 17 | Sat 8 Feb 2020 | 3-2 v WrexhamChesterfield 3-2 Wrexham | Vanarama National League |
| 18 | Sat 22 Feb 2020 | 4-0 v Ebbsfleet UnitedChesterfield 4-0 Ebbsfleet United | Vanarama National League |
| 19 | Sat 7 Mar 2020 | 2-1 v ChorleyChorley 1-2 Chesterfield | Vanarama National League |
| 20 | Sat 14 Mar 2020 | 1-1 v Dover AthleticDover Athletic 1-1 Chesterfield | Vanarama National League |
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