Middlesbrough FC in the Zenith Data Systems Cup
Competitions| 19-12-90 | Second Round | Manchester City | Away | 1 | 2 |
| 20-11-90 | First Round | Hull City | Home | 3 | 1 |
| 25-03-90 | Final | Chelsea | Neutral | 0 | 1 |
| 06-02-90 | Semi Final 2nd Leg | Aston Villa | Home | 2 | 1 |
| 30-01-90 | Second Round 1st Leg | Aston Villa | Away | 2 | 1 |
| 23-01-90 | Third Round | Newcastle United | Home | 1 | 0 |
| 20-12-89 | Second Round | Sheffield Wednesday | Home | 4 | 1 |
| 29-11-89 | First Round | Port Vale | Home | 3 | 1 |