| 1 | Tue 13 Aug 2019 | 2-3 v Blackburn RoversBlackburn Rovers 3-2 Oldham Athletic | Carabao Cup First Round |
| 2 | Sat 17 Aug 2019 | 0-3 v Bradford CityBradford City 3-0 Oldham Athletic | Sky Bet League Two |
| 3 | Tue 20 Aug 2019 | 0-0 v Exeter CityOldham Athletic 0-0 Exeter City | Sky Bet League Two |
| 4 | Sat 24 Aug 2019 | 2-1 v Cambridge UnitedCambridge United 1-2 Oldham Athletic | Sky Bet League Two |
| 5 | Sat 31 Aug 2019 | 0-1 v Colchester UnitedOldham Athletic 0-1 Colchester United | Sky Bet League Two |
| 6 | Sat 14 Sep 2019 | 2-2 v Grimsby TownOldham Athletic 2-2 Grimsby Town | Sky Bet League Two |
| 7 | Tue 17 Sep 2019 | 2-2 v Scunthorpe UnitedScunthorpe United 2-2 Oldham Athletic | Sky Bet League Two |
| 8 | Sat 28 Sep 2019 | 0-1 v Carlisle UnitedCarlisle United 1-0 Oldham Athletic | Sky Bet League Two |
| 9 | Sat 5 Oct 2019 | 1-1 v Cheltenham TownOldham Athletic 1-1 Cheltenham Town | Sky Bet League Two |
| 10 | Tue 8 Oct 2019 | 0-3 v Accrington StanleyOldham Athletic 0-3 Accrington Stanley | Leasing.com Trophy Northern Group B |
| 11 | Sat 12 Oct 2019 | 1-6 v Mansfield TownMansfield Town 6-1 Oldham Athletic | Sky Bet League Two |
| 12 | Sat 7 Dec 2019 | 1-1 v Leyton OrientOldham Athletic 1-1 Leyton Orient | Sky Bet League Two |
| 13 | Sat 14 Dec 2019 | 0-2 v Swindon TownSwindon Town 2-0 Oldham Athletic | Sky Bet League Two |
| 14 | Sun 29 Dec 2019 | 1-4 v Salford CityOldham Athletic 1-4 Salford City | Sky Bet League Two |
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