| Oldham Athletic FC v Chelsea FC 02/01/1999 | £5.50 | |
| Notts County FC v Oldham Athletic FC 09/01/1999 | View match | |
| Oldham Athletic FC v Blackpool FC 16/01/1999 | View match | |
| Fulham FC v Oldham Athletic FC 26/01/1999 | £1.50 | |
| York City FC v Oldham Athletic FC 30/01/1999 | View match | |
| Oldham Athletic FC v Lincoln City FC 06/02/1999 | View match | |
| Macclesfield Town FC v Oldham Athletic FC 13/02/1999 | View match | |
| Oldham Athletic FC v Northampton Town FC 20/02/1999 | View match | |
| Preston North End FC v Oldham Athletic FC 27/02/1999 | View match | |
| Oldham Athletic FC v AFC Bournemouth 06/03/1999 | View match | |
| Colchester United FC v Oldham Athletic FC 09/03/1999 | View match | |
| Manchester City FC v Oldham Athletic FC 13/03/1999 | £6.00 |