| 3. Round | 08/01/1988 | Sutton United | - | Middlesbrough FC | 1:1 | ||||
| 3. Round | 11/01/1988 | Middlesbrough FC | - | Sutton United | 1:0 aet |
| 3. Round | 08/01/1988 | Sutton United | - | Middlesbrough FC | 1:1 | ||||
| 3. Round | 11/01/1988 | Middlesbrough FC | - | Sutton United | 1:0 aet |
| Leonard Dennis | |
| Born: | 13.11.1964 |
| Place of birth: |
Lewisham, 
England |
| Nationality: |
Jamaica
England |
| Position(s): | Centre Forward |