| 1 | Sat 21 Sep 2019 | 3-1 v MorecambeOldham Athletic 3-1 Morecambe | Sky Bet League Two |
| 2 | Sat 5 Oct 2019 | 1-1 v Cheltenham TownOldham Athletic 1-1 Cheltenham Town | Sky Bet League Two |
| 3 | Tue 8 Oct 2019 | 0-3 v Accrington StanleyOldham Athletic 0-3 Accrington Stanley | Leasing.com Trophy Northern Group B |
| 4 | Sat 12 Oct 2019 | 1-6 v Mansfield TownMansfield Town 6-1 Oldham Athletic | Sky Bet League Two |
| 5 | Sat 19 Oct 2019 | 0-1 v Macclesfield TownOldham Athletic 0-1 Macclesfield Town | Sky Bet League Two |
| 6 | Tue 22 Oct 2019 | 2-0 v WalsallOldham Athletic 2-0 Walsall | Sky Bet League Two |
| 7 | Sat 26 Oct 2019 | 0-0 v Port ValePort Vale 0-0 Oldham Athletic | Sky Bet League Two |
| 8 | Sat 2 Nov 2019 | 2-2 v Northampton TownOldham Athletic 2-2 Northampton Town | Sky Bet League Two |
| 9 | Sun 10 Nov 2019 | 2-1 v GatesheadGateshead 1-2 Oldham Athletic | Emirates FA Cup First Round |
| 10 | Wed 13 Nov 2019 | 2-5 v Fleetwood TownFleetwood Town 5-2 Oldham Athletic | Leasing.com Trophy Northern Group B |
| 11 | Sat 23 Nov 2019 | 1-0 v Newport CountyNewport County 0-1 Oldham Athletic | Sky Bet League Two |
| 12 | Sat 30 Nov 2019 | 0-1 v Burton AlbionOldham Athletic 0-1 Burton Albion | Emirates FA Cup Second Round |
| 13 | Sat 7 Dec 2019 | 1-1 v Leyton OrientOldham Athletic 1-1 Leyton Orient | Sky Bet League Two |
| 14 | Sat 14 Dec 2019 | 0-2 v Swindon TownSwindon Town 2-0 Oldham Athletic | Sky Bet League Two |
| 15 | Sat 21 Dec 2019 | 2-1 v Crawley TownOldham Athletic 2-1 Crawley Town | Sky Bet League Two |
| 16 | Thu 26 Dec 2019 | 2-1 v MorecambeMorecambe 1-2 Oldham Athletic | Sky Bet League Two |
| 17 | Sun 29 Dec 2019 | 1-4 v Salford CityOldham Athletic 1-4 Salford City | Sky Bet League Two |
| 18 | Wed 1 Jan 2020 | 0-2 v Scunthorpe UnitedOldham Athletic 0-2 Scunthorpe United | Sky Bet League Two |
| 19 | Sat 11 Jan 2020 | 1-1 v Macclesfield TownMacclesfield Town 1-1 Oldham Athletic | Sky Bet League Two |
| 20 | Tue 14 Jan 2020 | 0-0 v StevenageStevenage 0-0 Oldham Athletic | Sky Bet League Two |
| 21 | Sat 1 Feb 2020 | 3-0 v Bradford CityOldham Athletic 3-0 Bradford City | Sky Bet League Two |
| 22 | Sat 8 Feb 2020 | 1-2 v Crewe AlexandraCrewe Alexandra 2-1 Oldham Athletic | Sky Bet League Two |
| 23 | Tue 11 Feb 2020 | 1-5 v Exeter CityExeter City 5-1 Oldham Athletic | Sky Bet League Two |
| 24 | Sat 15 Feb 2020 | 1-1 v Forest Green RoversOldham Athletic 1-1 Forest Green Rovers | Sky Bet League Two |
| 25 | Sat 22 Feb 2020 | 2-2 v Leyton OrientLeyton Orient 2-2 Oldham Athletic | 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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