| 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 31 Aug 2019 | 0-1 v Colchester UnitedOldham Athletic 0-1 Colchester United | Sky Bet League Two |
| 7 | Sat 28 Sep 2019 | 0-1 v Carlisle UnitedCarlisle United 1-0 Oldham Athletic | Sky Bet League Two |
| 8 | Sat 5 Oct 2019 | 1-1 v Cheltenham TownOldham Athletic 1-1 Cheltenham Town | Sky Bet League Two |
| 9 | Tue 8 Oct 2019 | 0-3 v Accrington StanleyOldham Athletic 0-3 Accrington Stanley | Leasing.com Trophy Northern Group B |
| 10 | Sat 19 Oct 2019 | 0-1 v Macclesfield TownOldham Athletic 0-1 Macclesfield Town | Sky Bet League Two |
| 11 | Tue 22 Oct 2019 | 2-0 v WalsallOldham Athletic 2-0 Walsall | Sky Bet League Two |
| 12 | Sat 26 Oct 2019 | 0-0 v Port ValePort Vale 0-0 Oldham Athletic | Sky Bet League Two |
| 13 | Sat 2 Nov 2019 | 2-2 v Northampton TownOldham Athletic 2-2 Northampton Town | Sky Bet League Two |
| 14 | Sun 10 Nov 2019 | 2-1 v GatesheadGateshead 1-2 Oldham Athletic | Emirates FA Cup First Round |
| 15 | Sat 7 Dec 2019 | 1-1 v Leyton OrientOldham Athletic 1-1 Leyton Orient | Sky Bet League Two |
| 16 | Sat 21 Dec 2019 | 2-1 v Crawley TownOldham Athletic 2-1 Crawley Town | Sky Bet League Two |
| 17 | Thu 26 Dec 2019 | 2-1 v MorecambeMorecambe 1-2 Oldham Athletic | Sky Bet League Two |
| 18 | Sun 29 Dec 2019 | 1-4 v Salford CityOldham Athletic 1-4 Salford City | Sky Bet League Two |
| 19 | Wed 1 Jan 2020 | 0-2 v Scunthorpe UnitedOldham Athletic 0-2 Scunthorpe United | Sky Bet League Two |
| 20 | Sat 11 Jan 2020 | 1-1 v Macclesfield TownMacclesfield Town 1-1 Oldham Athletic | Sky Bet League Two |
| 21 | Tue 14 Jan 2020 | 0-0 v StevenageStevenage 0-0 Oldham Athletic | Sky Bet League Two |
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