| 1. Round | 28/08/1937 | Portsmouth FC | - | West Bromwich Albion | 2:3 |  |
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| 2. Round | 01/09/1937 | Liverpool FC | - | Portsmouth FC | 3:2 | ||||
| 3. Round | 04/09/1937 | Birmingham FC | - | Portsmouth FC | 2:2 | ||||
| 4. Round | 08/09/1937 | Portsmouth FC | - | Liverpool FC | 1:1 | ||||
| 6. Round | 15/09/1937 | Leeds United | - | Portsmouth FC | 3:1 | ||||
| 7. Round | 18/09/1937 | Stoke City | - | Portsmouth FC | 3:1 | ||||
| 14. Round | 06/11/1937 | Portsmouth FC | - | Leicester City | 1:1 | ||||
| 38. Round | 16/04/1938 | Bolton Wanderers | - | Portsmouth FC | 1:1 |
England