2. Round | 10/08/1999 | Sunderland AFC | - | Watford FC | 2:0 | ||||
5. Round | 24/08/1999 | Watford FC | - | Aston Villa | 0:1 | ||||
6. Round | 30/08/1999 | Leicester City | - | Watford FC | 1:0 | ||||
7. Round | 11/09/1999 | West Ham United | - | Watford FC | 1:0 | ||||
13. Round | 31/10/1999 | Coventry City | - | Watford FC | 4:0 | ||||
19. Round | 26/12/1999 | Tottenham Hotspur | - | Watford FC | 4:0 | ||||
20. Round | 28/12/1999 | Watford FC | - | Southampton FC | 3:2 | ||||
33. Round | 15/04/2000 | Southampton FC | - | Watford FC | 2:0 | ||||
34. Round | 23/04/2000 | Watford FC | - | Arsenal FC | 2:3 |