| 1. Round | 02/09/1899 | Sunderland AFC | - | Aston Villa | 0:1 | ||||
| 33. Round | 04/09/1899 | Aston Villa | - | Glossop North End | 9:0 | ||||
| 2. Round | 09/09/1899 | Aston Villa | - | West Bromwich Albion | 0:2 | ||||
| 3. Round | 16/09/1899 | Everton FC | - | Aston Villa | 1:2 | ||||
| 4. Round | 23/09/1899 | Aston Villa | - | Blackburn Rovers | 3:1 | ||||
| 5. Round | 30/09/1899 | Derby County | - | Aston Villa | 2:0 | ||||
| 9. Round | 28/10/1899 | Sheffield United | - | Aston Villa | 2:1 | ||||
| 10. Round | 04/11/1899 | Aston Villa | - | Newcastle United | 2:1 | ||||
| 17. Round | 23/12/1899 | Aston Villa | - | Stoke City | 4:1 | ||||
| 18. Round | 30/12/1899 | Aston Villa | - | Sunderland AFC | 4:2 | ||||
| 19. Round | 01/01/1900 | Bury FC | - | Aston Villa | 2:0 | ||||
| 20. Round | 06/01/1900 | West Bromwich Albion | - | Aston Villa | 0:2 | ||||
| 21. Round | 13/01/1900 | Aston Villa | - | Everton FC | 1:1 | ||||
| 22. Round | 20/01/1900 | Blackburn Rovers | - | Aston Villa | 0:4 | ||||
| 23. Round | 03/02/1900 | Aston Villa | - | Derby County | 3:2 | ||||
| 24. Round | 17/02/1900 | Aston Villa | - | Notts County | 6:2 | ||||
| 29. Round | 24/03/1900 | Aston Villa | - | Liverpool FC | 1:0 |
England