1. Ronde | 27.08.1988 | Derby County | - | Middlesbrough FC | 1:0 | ||||
2. Ronde | 03.09.1988 | Middlesbrough FC | - | Norwich City | 2:3 | ||||
4. Ronde | 17.09.1988 | Middlesbrough FC | - | Wimbledon FC | 1:0 | ||||
5. Ronde | 24.09.1988 | Tottenham Hotspur | - | Middlesbrough FC | 3:2 |