| 3. Round | 05/01/1990 | Birmingham City | - | Oldham Athletic | 1:1 | ||||
| 3. Round | 09/01/1990 | Oldham Athletic | - | Birmingham City | 1:0 | ||||
| 4. Round | 26/01/1990 | Oldham Athletic | - | Brighton & Hove Albion | 2:1 | ||||
| Round of 16 | 16/02/1990 | Oldham Athletic | - | Everton FC | 2:2 | ||||
| Round of 16 | 20/02/1990 | Everton FC | - | Oldham Athletic | 1:1 aet | ||||
| Round of 16 | 09/03/1990 | Oldham Athletic | - | Everton FC | 2:1 aet | ||||
| Quarter-finals | 13/03/1990 | Oldham Athletic | - | Aston Villa | 3:0 | ||||
| Semi-finals | 08/04/1990 | Manchester United | - | Oldham Athletic | 3:3 aet | ||||
| Semi-finals | 11/04/1990 | Manchester United | - | Oldham Athletic | 2:1 aet |
England