1. Round | 15/08/1998 | Middlesbrough FC | - | Leeds United | 0:0 | ||||
2. Round | 23/08/1998 | Aston Villa | - | Middlesbrough FC | 3:1 | ||||
18. Round | 19/12/1998 | Manchester United | - | Middlesbrough FC | 2:3 | ||||
26. Round | 20/02/1999 | Middlesbrough FC | - | Tottenham Hotspur | 0:0 |