| 3. Round | 06/01/1989 | Blackpool FC | - | AFC Bournemouth | 0:1 | ||||
| 4. Round | 27/01/1989 | Hartlepool United | - | AFC Bournemouth | 1:1 | ||||
| 4. Round | 30/01/1989 | AFC Bournemouth | - | Hartlepool United | 5:2 | ||||
| Round of 16 | 17/02/1989 | AFC Bournemouth | - | Manchester United | 1:1 | ||||
| Round of 16 | 21/02/1989 | Manchester United | - | AFC Bournemouth | 1:0 |
England