| Birmingham City FC v Leyton Orient FC 11/11/1989 | View match | |
| Leyton Orient FC v Birmingham City FC 18/11/1989 | View match | |
| Leyton Orient FC v Mansfield Town FC 25/11/1989 | View match | |
| Leyton Orient FC v Mansfield Town FC 28/11/1989 | View match | |
| Brentford FC v Leyton Orient FC 03/12/1989 | View match | |
| Bristol City FC v Leyton Orient FC 16/12/1989 | View match | |
| Leyton Orient FC v Northampton Town FC 26/12/1989 | View match | |
| Leyton Orient FC v Crewe Alexandra FC 30/12/1989 | £5.00 | |
| Bury FC v Leyton Orient FC 01/01/1990 | £5.00 | |
| Chester City FC v Leyton Orient FC 06/01/1990 | View match | |
| Leyton Orient FC v Shrewsbury Town FC 13/01/1990 | View match | |
| Notts County FC v Leyton Orient FC 20/01/1990 | View match |