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 | ||||
6. Round | 15/09/1989 | Tottenham Hotspur | - | Chelsea FC | 1:4 | ||||
14. Round | 17/11/1989 | Crystal Palace | - | Tottenham Hotspur | 2:3 | ||||
19. Round | 25/12/1989 | Tottenham Hotspur | - | Millwall FC | 3:1 | ||||
20. Round | 29/12/1989 | Tottenham Hotspur | - | Nottingham Forest | 2:3 |