| 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 31 Aug 2019 | 1-1 v Dagenham & RedbridgeChesterfield 1-1 Dagenham & Redbridge | Vanarama National League |
| 8 | Tue 3 Sep 2019 | 2-3 v FC Halifax TownChesterfield 2-3 FC Halifax Town | Vanarama National League |
| 9 | Sat 7 Sep 2019 | 1-2 v BromleyBromley 2-1 Chesterfield | Vanarama National League |
| 10 | Sat 14 Sep 2019 | 1-0 v Torquay UnitedChesterfield 1-0 Torquay United | Vanarama National League |
| 11 | Sat 21 Sep 2019 | 0-4 v Sutton UnitedSutton United 4-0 Chesterfield | Vanarama National League |
| 12 | Sat 28 Sep 2019 | 2-1 v Aldershot TownChesterfield 2-1 Aldershot Town | Vanarama National League |
| 13 | Sat 5 Oct 2019 | 1-2 v EastleighChesterfield 1-2 Eastleigh | Vanarama National League |
| 14 | Sat 26 Oct 2019 | 1-0 v Notts CountyChesterfield 1-0 Notts County | Vanarama National League |
| 15 | Sat 2 Nov 2019 | 2-2 v Ebbsfleet UnitedEbbsfleet United 2-2 Chesterfield | Vanarama National League |
| 16 | Sat 16 Nov 2019 | 2-3 v ChorleyChesterfield 2-3 Chorley | Vanarama National League |
| 17 | Tue 26 Nov 2019 | 1-5 v Hartlepool UnitedChesterfield 1-5 Hartlepool United | Vanarama National League |
| 18 | Sat 30 Nov 2019 | 2-2 v Aldershot TownAldershot Town 2-2 Chesterfield | Vanarama National League |
| 19 | Sat 7 Dec 2019 | 1-2 v BromleyChesterfield 1-2 Bromley | Vanarama National League |
| 20 | Tue 10 Dec 2019 | 1-2 v Yeovil TownChesterfield 1-2 Yeovil Town | Vanarama National League |
| 21 | Sat 28 Dec 2019 | 0-1 v FC Halifax TownFC Halifax Town 1-0 Chesterfield | Vanarama National League |
| 22 | Wed 1 Jan 2020 | 0-3 v Solihull MoorsSolihull Moors 3-0 Chesterfield | Vanarama National League |
| 23 | Sat 4 Jan 2020 | 1-0 v Sutton UnitedChesterfield 1-0 Sutton United | Vanarama National League |
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