| 3. Round | 04/09/1937 | Birmingham FC | - | Portsmouth FC | 2:2 | ||||
| 4. Round | 08/09/1937 | Portsmouth FC | - | Liverpool FC | 1:1 | ||||
| 5. Round | 11/09/1937 | Portsmouth FC | - | Middlesbrough FC | 0:2 | ||||
| 6. Round | 15/09/1937 | Leeds United | - | Portsmouth FC | 3:1 | ||||
| 7. Round | 18/09/1937 | Stoke City | - | Portsmouth FC | 3:1 | ||||
| 10. Round | 09/10/1937 | Charlton Athletic | - | Portsmouth FC | 5:1 | ||||
| 11. Round | 16/10/1937 | Arsenal FC | - | Portsmouth FC | 1:1 | ||||
| 12. Round | 23/10/1937 | Portsmouth FC | - | Blackpool FC | 1:2 | ||||
| 13. Round | 30/10/1937 | Brentford FC | - | Portsmouth FC | 2:0 | ||||
| 14. Round | 06/11/1937 | Portsmouth FC | - | Leicester City | 1:1 | ||||
| 15. Round | 13/11/1937 | Huddersfield Town | - | Portsmouth FC | 2:0 |
England