1. Round | 07/08/1999 | Watford FC | - | Wimbledon FC | 2:3 | ||||
2. Round | 10/08/1999 | Sunderland AFC | - | Watford FC | 2:0 | ||||
3. Round | 14/08/1999 | Liverpool FC | - | Watford FC | 0:1 | ||||
4. Round | 21/08/1999 | Watford FC | - | Bradford City | 1:0 | ||||
5. Round | 24/08/1999 | Watford FC | - | Aston Villa | 0:1 | ||||
6. Round | 30/08/1999 | Leicester City | - | Watford FC | 1:0 | ||||
24. Round | 05/02/2000 | Aston Villa | - | Watford FC | 4:0 | ||||
25. Round | 12/02/2000 | Watford FC | - | Leicester City | 1:1 | ||||
35. Round | 03/05/2000 | Leeds United | - | Watford FC | 3:1 | ||||
37. Round | 06/05/2000 | Middlesbrough FC | - | Watford FC | 1:1 | ||||
38. Round | 14/05/2000 | Watford FC | - | Coventry City | 1:0 |