10. Round | 24/10/1998 | Tottenham Hotspur | - | Newcastle United | 2:0 | ||||
11. Round | 02/11/1998 | Tottenham Hotspur | - | Charlton Athletic | 2:2 | ||||
12. Round | 07/11/1998 | Aston Villa | - | Tottenham Hotspur | 3:2 | ||||
13. Round | 14/11/1998 | Arsenal FC | - | Tottenham Hotspur | 0:0 | ||||
14. Round | 21/11/1998 | Tottenham Hotspur | - | Nottingham Forest | 2:0 | ||||
37. Round | 10/05/1999 | Tottenham Hotspur | - | Chelsea FC | 2:2 | ||||
38. Round | 16/05/1999 | Manchester United | - | Tottenham Hotspur | 2:1 |