| 13. Round | 25/11/1899 | Aston Villa | - | Burnley FC | 2:0 | ||||
| 14. Round | 02/12/1899 | Preston North End | - | Aston Villa | 0:5 | ||||
| 15. Round | 09/12/1899 | Aston Villa | - | Nottingham Forest | 2:2 | ||||
| 16. Round | 16/12/1899 | Glossop North End | - | Aston Villa | 1:0 | ||||
| 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 | ||||
| 26. Round | 03/03/1900 | Aston Villa | - | Sheffield United | 1:1 | ||||
| 27. Round | 10/03/1900 | Newcastle United | - | Aston Villa | 3:2 | ||||
| 30. Round | 31/03/1900 | Burnley FC | - | Aston Villa | 1:2 | ||||
| 31. Round | 07/04/1900 | Aston Villa | - | Preston North End | 3:1 | ||||
| 28. Round | 16/04/1900 | Wolverhampton Wanderers | - | Aston Villa | 0:1 |
England