| 3. Round | 10/12/1999 | Aston Villa | - | Darlington FC | 2:1 | ||||
| 4. Round | 07/01/2000 | Aston Villa | - | Southampton FC | 1:0 | ||||
| Round of 16 | 30/01/2000 | Aston Villa | - | Leeds United | 3:2 | ||||
| Quarter-finals | 20/02/2000 | Everton FC | - | Aston Villa | 1:2 | ||||
| Semi-finals | 02/04/2000 | Bolton Wanderers | - | Aston Villa | 1:4 pso | ||||
| Final | 20/05/2000 | Aston Villa | - | Chelsea FC | 0:1 |
England