| 3. Round | 06/01/1989 | Manchester United | - | Queens Park Rangers | 0:0 | ||||
| 3. Round | 10/01/1989 | Queens Park Rangers | - | Manchester United | 2:2 aet | ||||
| 3. Round | 22/01/1989 | Manchester United | - | Queens Park Rangers | 3:0 | ||||
| 4. Round | 27/01/1989 | Manchester United | - | Oxford United | 4:0 | ||||
| Round of 16 | 17/02/1989 | AFC Bournemouth | - | Manchester United | 1:1 | ||||
| Round of 16 | 21/02/1989 | Manchester United | - | AFC Bournemouth | 1:0 | ||||
| Quarter-finals | 18/03/1989 | Manchester United | - | Nottingham Forest | 0:1 |
Scotland