 |
 |
| Pr. League | 02.01.1989 | Middlesbrough FC | - | Manchester United | 1:0 | 24.411 |
| FA Cup | 07.01.1989 | Middlesbrough FC | - | Grimsby Town | 1:2 | 19.190 |
| Pr. League | 21.01.1989 | Middlesbrough FC | - | Tottenham Hotspur | 2:2 | 23.692 |
| Pr. League | 04.02.1989 | Middlesbrough FC | - | Coventry City | 1:1 | 17.352 |
| Pr. League | 26.02.1989 | Middlesbrough FC | - | Newcastle United | 1:1 | 24.385 |
| Pr. League | 11.03.1989 | Middlesbrough FC | - | Liverpool FC | 0:4 | 25.197 |
| Pr. League | 18.03.1989 | Middlesbrough FC | - | Derby County | 0:1 | 16.580 |
| Pr. League | 27.03.1989 | Middlesbrough FC | - | Everton FC | 3:3 | 21.351 |
| Pr. League | 08.04.1989 | Middlesbrough FC | - | Southampton FC | 3:3 | 16.983 |
| Pr. League | 22.04.1989 | Middlesbrough FC | - | Nottingham Forest | 3:4 | 20.778 |
| Pr. League | 06.05.1989 | Middlesbrough FC | - | Arsenal FC | 0:1 | 21.803 |
| League Cup | 20.09.1989 | Middlesbrough FC | - | Halifax Town | 4:0 | 10.613 |
England