| 1 | Sat 3 Aug 2019 | 0-1 v Forest Green RoversForest Green Rovers 1-0 Oldham Athletic | Sky Bet League Two |
| 2 | Sat 10 Aug 2019 | 1-2 v Crewe AlexandraOldham Athletic 1-2 Crewe Alexandra | Sky Bet League Two |
| 3 | Tue 13 Aug 2019 | 2-3 v Blackburn RoversBlackburn Rovers 3-2 Oldham Athletic | Carabao Cup First Round |
| 4 | Sat 17 Aug 2019 | 0-3 v Bradford CityBradford City 3-0 Oldham Athletic | Sky Bet League Two |
| 5 | Tue 20 Aug 2019 | 0-0 v Exeter CityOldham Athletic 0-0 Exeter City | Sky Bet League Two |
| 6 | Sat 24 Aug 2019 | 2-1 v Cambridge UnitedCambridge United 1-2 Oldham Athletic | Sky Bet League Two |
| 7 | Sat 31 Aug 2019 | 0-1 v Colchester UnitedOldham Athletic 0-1 Colchester United | Sky Bet League Two |
| 8 | Sat 14 Sep 2019 | 2-2 v Grimsby TownOldham Athletic 2-2 Grimsby Town | Sky Bet League Two |
| 9 | Tue 17 Sep 2019 | 2-2 v Scunthorpe UnitedScunthorpe United 2-2 Oldham Athletic | Sky Bet League Two |
| 10 | Sat 28 Sep 2019 | 0-1 v Carlisle UnitedCarlisle United 1-0 Oldham Athletic | Sky Bet League Two |
| 11 | Sat 12 Oct 2019 | 1-6 v Mansfield TownMansfield Town 6-1 Oldham Athletic | Sky Bet League Two |
| 12 | Sat 11 Jan 2020 | 1-1 v Macclesfield TownMacclesfield Town 1-1 Oldham Athletic | Sky Bet League Two |
| 13 | Tue 14 Jan 2020 | 0-0 v StevenageStevenage 0-0 Oldham Athletic | Sky Bet League Two |
| 14 | Sat 15 Feb 2020 | 1-1 v Forest Green RoversOldham Athletic 1-1 Forest Green Rovers | Sky Bet League Two |
| 15 | Sat 22 Feb 2020 | 2-2 v Leyton OrientLeyton Orient 2-2 Oldham Athletic | Sky Bet League Two |
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