| 1. Round | 31/08/1929 | Derby County | - | Sunderland AFC | 3:0 | ||||
| 6. Round | 21/09/1929 | Sunderland AFC | - | Arsenal FC | 0:1 | ||||
| 9. Round | 05/10/1929 | Sunderland AFC | - | Leeds United | 1:4 | ||||
| 13. Round | 02/11/1929 | Sunderland AFC | - | Huddersfield Town | 1:0 | ||||
| 14. Round | 09/11/1929 | Middlesbrough FC | - | Sunderland AFC | 3:0 | ||||
| 15. Round | 16/11/1929 | Sunderland AFC | - | Leicester City | 2:1 | ||||
| 16. Round | 23/11/1929 | Grimsby Town | - | Sunderland AFC | 0:1 | ||||
| 17. Round | 30/11/1929 | Sunderland AFC | - | Manchester United | 2:4 | ||||
| 18. Round | 07/12/1929 | West Ham United | - | Sunderland AFC | 1:1 |  |
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| 19. Round | 14/12/1929 | Sunderland AFC | - | Liverpool FC | 2:3 |
Scotland