| 1. Round | 09/09/1908 | Middlesbrough FC | - | Sunderland AFC | 0:3 | ||||
| 3. Round | 12/09/1908 | Sunderland AFC | - | Sheffield United | 3:1 | ||||
| 5. Round | 26/09/1908 | Sunderland AFC | - | Nottingham Forest | 2:1 | ||||
| 6. Round | 03/10/1908 | Sunderland AFC | - | The Wednesday FC | 4:2 | ||||
| 15. Round | 05/12/1908 | Newcastle United | - | Sunderland AFC | 1:9 | ||||
| 17. Round | 19/12/1908 | Preston North End | - | Sunderland AFC | 1:0 | ||||
| 36. Round | 26/12/1908 | Sunderland AFC | - | Middlesbrough FC | 2:0 | ||||
| 21. Round | 09/01/1909 | Sheffield United | - | Sunderland AFC | 0:2 | ||||
| 22. Round | 23/01/1909 | Sunderland AFC | - | Aston Villa | 4:3 | ||||
| 23. Round | 30/01/1909 | Nottingham Forest | - | Sunderland AFC | 4:0 | ||||
| 27. Round | 27/02/1909 | Sunderland AFC | - | Bradford City | 2:1 | ||||
| 29. Round | 13/03/1909 | Sunderland AFC | - | Everton FC | 2:0 | ||||
| 28. Round | 15/03/1909 | Manchester United | - | Sunderland AFC | 2:2 | ||||
| 30. Round | 20/03/1909 | Leicester Fosse | - | Sunderland AFC | 4:3 | ||||
| 34. Round | 10/04/1909 | Sunderland AFC | - | Newcastle United | 3:1 | ||||
| 35. Round | 12/04/1909 | Liverpool FC | - | Sunderland AFC | 3:0 | ||||
| 37. Round | 17/04/1909 | Bristol City | - | Sunderland AFC | 2:4 |
England