| 1 | 10/8/2019 | 1-2 v Crewe AlexandraOldham Athletic 1-2 Crewe Alexandra | Sky Bet League Two |
| 2 | 13/8/2019 | 2-3 v Blackburn RoversBlackburn Rovers 3-2 Oldham Athletic | Carabao Cup First Round |
| 3 | 17/8/2019 | 0-3 v Bradford CityBradford City 3-0 Oldham Athletic | Sky Bet League Two |
| 4 | 20/8/2019 | 0-0 v Exeter CityOldham Athletic 0-0 Exeter City | Sky Bet League Two |
| 5 | 24/8/2019 | 2-1 v Cambridge UnitedCambridge United 1-2 Oldham Athletic | Sky Bet League Two |
| 6 | 31/8/2019 | 0-1 v Colchester UnitedOldham Athletic 0-1 Colchester United | Sky Bet League Two |
| 7 | 14/9/2019 | 2-2 v Grimsby TownOldham Athletic 2-2 Grimsby Town | Sky Bet League Two |
| 8 | 17/9/2019 | 2-2 v Scunthorpe UnitedScunthorpe United 2-2 Oldham Athletic | Sky Bet League Two |
| 9 | 21/9/2019 | 3-1 v MorecambeOldham Athletic 3-1 Morecambe | Sky Bet League Two |
| 10 | 28/9/2019 | 0-1 v Carlisle UnitedCarlisle United 1-0 Oldham Athletic | Sky Bet League Two |
| 11 | 5/10/2019 | 1-1 v Cheltenham TownOldham Athletic 1-1 Cheltenham Town | Sky Bet League Two |
| 12 | 8/10/2019 | 0-3 v Accrington StanleyOldham Athletic 0-3 Accrington Stanley | Checkatrade Trophy Northern Group B |
| 13 | 12/10/2019 | 1-6 v Mansfield TownMansfield Town 6-1 Oldham Athletic | Sky Bet League Two |
| 14 | 2/11/2019 | 2-2 v Northampton TownOldham Athletic 2-2 Northampton Town | Sky Bet League Two |
| 15 | 10/11/2019 | 2-1 v GatesheadGateshead 1-2 Oldham Athletic | Emirates FA Cup First Round |
| 16 | 23/11/2019 | 1-0 v Newport CountyNewport County 0-1 Oldham Athletic | Sky Bet League Two |
| 17 | 30/11/2019 | 0-1 v Burton AlbionOldham Athletic 0-1 Burton Albion | Emirates FA Cup Second Round |
| 18 | 7/12/2019 | 1-1 v Leyton OrientOldham Athletic 1-1 Leyton Orient | Sky Bet League Two |
| 19 | 14/12/2019 | 0-2 v Swindon TownSwindon Town 2-0 Oldham Athletic | Sky Bet League Two |
| 20 | 21/12/2019 | 2-1 v Crawley TownOldham Athletic 2-1 Crawley Town | Sky Bet League Two |
| 21 | 26/12/2019 | 2-1 v MorecambeMorecambe 1-2 Oldham Athletic | Sky Bet League Two |
| 22 | 29/12/2019 | 1-4 v Salford CityOldham Athletic 1-4 Salford City | Sky Bet League Two |
| 23 | 1/1/2020 | 0-2 v Scunthorpe UnitedOldham Athletic 0-2 Scunthorpe United | Sky Bet League Two |
| 24 | 11/1/2020 | 1-1 v Macclesfield TownMacclesfield Town 1-1 Oldham Athletic | Sky Bet League Two |
