| 1 | Sat 3 Aug 2019 | 161-2 v Dover AthleticChesterfield 1-2 Dover Athletic | Vanarama National League |
| 2 | Tue 6 Aug 2019 | 161-1 v Maidenhead UnitedMaidenhead United 1-1 Chesterfield | Vanarama National League |
| 3 | Sat 10 Aug 2019 | 162-2 v Boreham WoodBoreham Wood 2-2 Chesterfield | Vanarama National League |
| 4 | Tue 13 Aug 2019 | 161-2 v WokingChesterfield 1-2 Woking | Vanarama National League |
| 5 | Sat 31 Aug 2019 | 161-1 v Dagenham & RedbridgeChesterfield 1-1 Dagenham & Redbridge | Vanarama National League |
| 6 | Tue 3 Sep 2019 | 162-3 v FC Halifax TownChesterfield 2-3 FC Halifax Town | Vanarama National League |
| 7 | Sat 14 Sep 2019 | 161-0 v Torquay UnitedChesterfield 1-0 Torquay United | Vanarama National League |
| 8 | Sat 21 Sep 2019 | 160-4 v Sutton UnitedSutton United 4-0 Chesterfield | Vanarama National League |
| 9 | Tue 24 Sep 2019 | 161-1 v Hartlepool UnitedHartlepool United 1-1 Chesterfield | Vanarama National League |
| 10 | Sat 28 Sep 2019 | 162-1 v Aldershot TownChesterfield 2-1 Aldershot Town | Vanarama National League |
| 11 | Sat 5 Oct 2019 | 161-2 v EastleighChesterfield 1-2 Eastleigh | Vanarama National League |
| 12 | Tue 8 Oct 2019 | 163-1 v AFC FyldeAFC Fylde 1-3 Chesterfield | Vanarama National League |
| 13 | Sat 26 Oct 2019 | 161-0 v Notts CountyChesterfield 1-0 Notts County | Vanarama National League |
| 14 | Sat 2 Nov 2019 | 162-2 v Ebbsfleet UnitedEbbsfleet United 2-2 Chesterfield | Vanarama National League |
| 15 | Sat 16 Nov 2019 | 162-3 v ChorleyChesterfield 2-3 Chorley | Vanarama National League |
| 16 | Tue 26 Nov 2019 | 161-5 v Hartlepool UnitedChesterfield 1-5 Hartlepool United | Vanarama National League |
| 17 | Sat 14 Dec 2019 | 160-1 v Notts CountyChesterfield 0-1 Notts County | Buildbase FA Trophy First Round |
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