| Chester City FC v Leyton Orient FC 15/09/1990 | View match | |
| Tranmere Rovers FC v Leyton Orient FC 17/09/1990 | View match | |
| Leyton Orient FC v Rotherham United FC 22/09/1990 | View match | |
| Charlton Athletic FC v Leyton Orient FC 26/09/1990 | £4.50 | |
| Leyton Orient FC v Bradford City FC 29/09/1990 | £5.00 | |
| Cambridge United FC v Leyton Orient FC 02/10/1990 | View match | |
| Huddersfield Town FC v Leyton Orient FC 06/10/1990 | View match | |
| Leyton Orient FC v Charlton Athletic FC 09/10/1990 | £5.00 | |
| Leyton Orient FC v Shrewsbury Town FC 13/10/1990 | View match | |
| Leyton Orient FC v Bolton Wanderers FC 20/10/1990 | View match | |
| Grimsby Town FC v Leyton Orient FC 23/10/1990 | View match | |
| Reading FC v Leyton Orient FC 27/10/1990 | View match |