Middlesbrough FC in the Simod Cup
Competitions| 28-01-89 | Fourth Round | Crystal Palace | Home | 2 | 3 |
| 11-01-89 | Third Round | Coventry City | Home | 1 | 0 |
| 21-12-88 | Second Round | Portsmouth | Home | 2 | 1 |
| 14-12-88 | First Round | Oldham Athletic | Home | 1 | 0 |
| 10-11-87 | First Round | Ipswich Town | Away | 0 | 1 |