1. Round | 18/08/1989 | Tottenham Hotspur | - | Luton Town | 2:1 | ||||
2. Round | 21/08/1989 | Everton FC | - | Tottenham Hotspur | 2:1 | ||||
3. Round | 25/08/1989 | Manchester City | - | Tottenham Hotspur | 1:1 | ||||
5. Round | 08/09/1989 | Aston Villa | - | Tottenham Hotspur | 2:0 | ||||
7. Round | 22/09/1989 | Norwich City | - | Tottenham Hotspur | 2:2 | ||||
8. Round | 30/09/1989 | Tottenham Hotspur | - | Queens Park Rangers | 3:2 | ||||
9. Round | 14/10/1989 | Charlton Athletic | - | Tottenham Hotspur | 1:3 |