| 1. Ronde | 02.09.1899 | Sunderland AFC | - | Aston Villa | 0:1 | ||||
| 33. Ronde | 04.09.1899 | Aston Villa | - | Glossop North End | 9:0 | ||||
| 2. Ronde | 09.09.1899 | Aston Villa | - | West Bromwich Albion | 0:2 | ||||
| 3. Ronde | 16.09.1899 | Everton FC | - | Aston Villa | 1:2 | ||||
| 4. Ronde | 23.09.1899 | Aston Villa | - | Blackburn Rovers | 3:1 | ||||
| 5. Ronde | 30.09.1899 | Derby County | - | Aston Villa | 2:0 | ||||
| 9. Ronde | 28.10.1899 | Sheffield United | - | Aston Villa | 2:1 | ||||
| 10. Ronde | 04.11.1899 | Aston Villa | - | Newcastle United | 2:1 | ||||
| 17. Ronde | 23.12.1899 | Aston Villa | - | Stoke City | 4:1 | ||||
| 18. Ronde | 30.12.1899 | Aston Villa | - | Sunderland AFC | 4:2 | ||||
| 19. Ronde | 01.01.1900 | Bury FC | - | Aston Villa | 2:0 | ||||
| 20. Ronde | 06.01.1900 | West Bromwich Albion | - | Aston Villa | 0:2 | ||||
| 21. Ronde | 13.01.1900 | Aston Villa | - | Everton FC | 1:1 | ||||
| 22. Ronde | 20.01.1900 | Blackburn Rovers | - | Aston Villa | 0:4 | ||||
| 23. Ronde | 03.02.1900 | Aston Villa | - | Derby County | 3:2 | ||||
| 24. Ronde | 17.02.1900 | Aston Villa | - | Notts County | 6:2 | ||||
| 29. Ronde | 24.03.1900 | Aston Villa | - | Liverpool FC | 1:0 |
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