1. Round | 26/08/1988 | Derby County | - | Middlesbrough FC | 1:0 | ||||
2. Round | 02/09/1988 | Middlesbrough FC | - | Norwich City | 2:3 | ||||
4. Round | 16/09/1988 | Middlesbrough FC | - | Wimbledon FC | 1:0 | ||||
5. Round | 23/09/1988 | Tottenham Hotspur | - | Middlesbrough FC | 3:2 |