 |
 |
| FA Cup | 12.01.1988 | Middlesbrough FC | - | Sutton United | 1:0 n.V. | 17.932 |
| FA Cup | 03.02.1988 | Middlesbrough FC | - | Everton FC | 2:2 n.V. | 25.235 |
| Pr. League | 03.09.1988 | Middlesbrough FC | - | Norwich City | 2:3 | 18.259 |
| Pr. League | 17.09.1988 | Middlesbrough FC | - | Wimbledon FC | 1:0 | 17.709 |
| League Cup | 28.09.1988 | Middlesbrough FC | - | Tranmere Rovers | 0:0 | 12.084 |
| Pr. League | 08.10.1988 | Middlesbrough FC | - | West Ham United | 1:0 | 19.608 |
| Pr. League | 22.10.1988 | Middlesbrough FC | - | Luton Town | 2:1 | 17.792 |
| Pr. League | 29.10.1988 | Middlesbrough FC | - | Millwall FC | 4:2 | 19.788 |
| Pr. League | 12.11.1988 | Middlesbrough FC | - | Queens Park Rangers | 1:0 | 20.565 |
| Pr. League | 26.11.1988 | Middlesbrough FC | - | Sheffield Wednesday | 0:1 | 19.310 |
| Pr. League | 10.12.1988 | Middlesbrough FC | - | Aston Villa | 3:3 | 18.096 |
| Pr. League | 17.12.1988 | Middlesbrough FC | - | Charlton Athletic | 0:0 | 16.065 |
England