| 1 | Sat 14 Sep 2019 | 301-0 v Torquay UnitedChesterfield 1-0 Torquay United | Vanarama National League |
| 2 | Tue 24 Sep 2019 | 301-1 v Hartlepool UnitedHartlepool United 1-1 Chesterfield | Vanarama National League |
| 3 | Sat 28 Sep 2019 | 302-1 v Aldershot TownChesterfield 2-1 Aldershot Town | Vanarama National League |
| 4 | Sat 5 Oct 2019 | 301-2 v EastleighChesterfield 1-2 Eastleigh | Vanarama National League |
| 5 | Tue 8 Oct 2019 | 303-1 v AFC FyldeAFC Fylde 1-3 Chesterfield | Vanarama National League |
| 6 | Sat 26 Oct 2019 | 301-0 v Notts CountyChesterfield 1-0 Notts County | Vanarama National League |
| 7 | Sat 16 Nov 2019 | 302-3 v ChorleyChesterfield 2-3 Chorley | Vanarama National League |
| 8 | Tue 26 Nov 2019 | 301-5 v Hartlepool UnitedChesterfield 1-5 Hartlepool United | Vanarama National League |
| 9 | Sat 14 Dec 2019 | 300-1 v Notts CountyChesterfield 0-1 Notts County | Buildbase FA Trophy First Round |
| 10 | Sat 8 Feb 2020 | 303-2 v WrexhamChesterfield 3-2 Wrexham | Vanarama National League |
| 11 | Sat 22 Feb 2020 | 304-0 v Ebbsfleet UnitedChesterfield 4-0 Ebbsfleet United | Vanarama National League |
| 12 | Sat 7 Mar 2020 | 302-1 v ChorleyChorley 1-2 Chesterfield | Vanarama National League |
| 13 | Sat 14 Mar 2020 | 301-1 v Dover AthleticDover Athletic 1-1 Chesterfield | Vanarama National League |
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