| 1 | Sat 10 Aug 2019 | 271-2 v Crewe AlexandraOldham Athletic 1-2 Crewe Alexandra | Sky Bet League Two |
| 2 | Tue 13 Aug 2019 | 272-3 v Blackburn RoversBlackburn Rovers 3-2 Oldham Athletic | Carabao Cup First Round |
| 3 | Sat 17 Aug 2019 | 270-3 v Bradford CityBradford City 3-0 Oldham Athletic | Sky Bet League Two |
| 4 | Tue 20 Aug 2019 | 270-0 v Exeter CityOldham Athletic 0-0 Exeter City | Sky Bet League Two |
| 5 | Sat 24 Aug 2019 | 272-1 v Cambridge UnitedCambridge United 1-2 Oldham Athletic | Sky Bet League Two |
| 6 | Sat 21 Sep 2019 | 0-4 v Sutton UnitedSutton United 4-0 Chesterfield | Vanarama National League |
| 7 | Tue 24 Sep 2019 | 1-1 v Hartlepool UnitedHartlepool United 1-1 Chesterfield | Vanarama National League |
| 8 | Sat 28 Sep 2019 | 2-1 v Aldershot TownChesterfield 2-1 Aldershot Town | Vanarama National League |
| 9 | Sat 5 Oct 2019 | 1-2 v EastleighChesterfield 1-2 Eastleigh | Vanarama National League |
| 10 | Sat 26 Oct 2019 | 1-0 v Notts CountyChesterfield 1-0 Notts County | Vanarama National League |
| 11 | Sat 2 Nov 2019 | 2-2 v Ebbsfleet UnitedEbbsfleet United 2-2 Chesterfield | Vanarama National League |
| 12 | Sat 23 Nov 2019 | 1-3 v Harrogate TownHarrogate Town 3-1 Chesterfield | Vanarama National League |
| 13 | Tue 26 Nov 2019 | 1-5 v Hartlepool UnitedChesterfield 1-5 Hartlepool United | Vanarama National League |
| 14 | Sat 30 Nov 2019 | 2-2 v Aldershot TownAldershot Town 2-2 Chesterfield | Vanarama National League |
| 15 | Sat 7 Dec 2019 | 1-2 v BromleyChesterfield 1-2 Bromley | Vanarama National League |
| 16 | Tue 10 Dec 2019 | 1-2 v Yeovil TownChesterfield 1-2 Yeovil Town | Vanarama National League |
| 17 | Sat 14 Dec 2019 | 0-1 v Notts CountyChesterfield 0-1 Notts County | Buildbase FA Trophy First Round |
| 18 | Sat 21 Dec 2019 | 3-0 v Torquay UnitedTorquay United 0-3 Chesterfield | Vanarama National League |
| 19 | Thu 26 Dec 2019 | 2-2 v Solihull MoorsChesterfield 2-2 Solihull Moors | Vanarama National League |
| 20 | Sat 28 Dec 2019 | 0-1 v FC Halifax TownFC Halifax Town 1-0 Chesterfield | Vanarama National League |
| 21 | Sat 11 Jan 2020 | 1-1 v Macclesfield TownMacclesfield Town 1-1 Oldham Athletic | Sky Bet League Two |
| 22 | Tue 14 Jan 2020 | 0-0 v StevenageStevenage 0-0 Oldham Athletic | Sky Bet League Two |
| 23 | Sat 1 Feb 2020 | 3-0 v Bradford CityOldham Athletic 3-0 Bradford City | Sky Bet League Two |
| 24 | Sat 8 Feb 2020 | 1-2 v Crewe AlexandraCrewe Alexandra 2-1 Oldham Athletic | Sky Bet League Two |
| 25 | Sat 15 Feb 2020 | 1-1 v Forest Green RoversOldham Athletic 1-1 Forest Green Rovers | Sky Bet League Two |
| 26 | Sat 29 Feb 2020 | 5-0 v Newport CountyOldham Athletic 5-0 Newport County | Sky Bet League Two |
| 27 | Sat 7 Mar 2020 | 0-3 v Crawley TownCrawley Town 3-0 Oldham Athletic | Sky Bet League Two |
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