| 4. Round | 11/09/1929 | Portsmouth FC | - | Grimsby Town | 1:1 | ||||
| 5. Round | 14/09/1929 | Portsmouth FC | - | Sunderland AFC | 1:1 | ||||
| 6. Round | 21/09/1929 | Bolton Wanderers | - | Portsmouth FC | 2:1 |  |
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| 7. Round | 23/09/1929 | Leeds United | - | Portsmouth FC | 1:0 | ||||
| 8. Round | 28/09/1929 | Portsmouth FC | - | Everton FC | 1:4 | ||||
| 9. Round | 05/10/1929 | Derby County | - | Portsmouth FC | 3:2 | ||||
| 10. Round | 12/10/1929 | Portsmouth FC | - | Manchester City | 2:2 |
Scotland