| 1 | Sat 12 Jan 2019 | 0-0 v Forest Green RoversOldham Athletic 0-0 Forest Green Rovers | Sky Bet League Two |
| 2 | Sat 19 Jan 2019 | 1-2 v Macclesfield TownMacclesfield Town 2-1 Oldham Athletic | Sky Bet League Two |
| 3 | Sat 26 Jan 2019 | 1-2 v Doncaster RoversDoncaster Rovers 2-1 Oldham Athletic | Emirates FA Cup Fourth Round |
| 4 | Tue 29 Jan 2019 | 1-2 v Milton Keynes DonsMilton Keynes Dons 2-1 Oldham Athletic | Sky Bet League Two |
| 5 | Sat 9 Feb 2019 | 3-0 v Crawley TownCrawley Town 0-3 Oldham Athletic | Sky Bet League Two |
| 6 | Tue 12 Feb 2019 | 4-1 v Yeovil TownOldham Athletic 4-1 Yeovil Town | Sky Bet League Two |
| 7 | Sat 16 Feb 2019 | 1-1 v Crewe AlexandraOldham Athletic 1-1 Crewe Alexandra | Sky Bet League Two |
| 8 | Tue 19 Feb 2019 | 1-2 v MorecambeOldham Athletic 1-2 Morecambe | Sky Bet League Two |
| 9 | Tue 2 Apr 2019 | 2-0 v Tranmere RoversOldham Athletic 2-0 Tranmere Rovers | Sky Bet League Two |
| 10 | Sat 6 Apr 2019 | 2-0 v Colchester UnitedColchester United 0-2 Oldham Athletic | Sky Bet League Two |
| 11 | Sat 13 Apr 2019 | 2-2 v Swindon TownOldham Athletic 2-2 Swindon Town | Sky Bet League Two |
| 12 | Fri 19 Apr 2019 | 0-0 v Cheltenham TownCheltenham Town 0-0 Oldham Athletic | Sky Bet League Two |
| 13 | Mon 22 Apr 2019 | 3-2 v Mansfield TownOldham Athletic 3-2 Mansfield Town | Sky Bet League Two |
| 14 | Sat 27 Apr 2019 | 0-1 v Exeter CityExeter City 1-0 Oldham Athletic | Sky Bet League Two |
| 15 | Tue 30 Apr 2019 | 0-2 v Newport CountyNewport County 2-0 Oldham Athletic | Sky Bet League Two |
| 16 | Sat 4 May 2019 | 2-5 v Northampton TownOldham Athletic 2-5 Northampton Town | Sky Bet League Two |
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