| 2. Round | 06/09/1938 | Grimsby Town | - | Portsmouth FC | 2:1 |  |
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| 5. Round | 10/09/1938 | Portsmouth FC | - | Huddersfield Town | 4:0 | ||||
| 6. Round | 17/09/1938 | Everton FC | - | Portsmouth FC | 5:1 | |
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| 15. Round | 19/11/1938 | Portsmouth FC | - | Middlesbrough FC | 1:1 | ||||
| 18. Round | 10/12/1938 | Stoke City | - | Portsmouth FC | 1:1 | ||||
| 19. Round | 17/12/1938 | Portsmouth FC | - | Chelsea FC | 2:1 | ||||
| 20. Round | 24/12/1938 | Portsmouth FC | - | Arsenal FC | 0:0 | ||||
| 22. Round | 27/12/1938 | Portsmouth FC | - | Brentford FC | 2:2 | ||||
| 23. Round | 31/12/1938 | Bolton Wanderers | - | Portsmouth FC | 5:1 | ||||
| 26. Round | 28/01/1939 | Wolverhampton Wanderers | - | Portsmouth FC | 3:0 | ||||
| 25. Round | 01/02/1939 | Portsmouth FC | - | Everton FC | 0:1 | ||||
| 27. Round | 04/02/1939 | Portsmouth FC | - | Aston Villa | 0:0 | ||||
| 29. Round | 18/02/1939 | Portsmouth FC | - | Preston North End | 0:0 | ||||
| 21. Round | 22/02/1939 | Brentford FC | - | Portsmouth FC | 2:0 | ||||
| 37. Round | 08/04/1939 | Manchester United | - | Portsmouth FC | 1:1 | ||||
| 38. Round | 10/04/1939 | Derby County | - | Portsmouth FC | 0:1 | ||||
| 39. Round | 15/04/1939 | Portsmouth FC | - | Stoke City | 2:0 | ||||
| 41. Round | 19/04/1939 | Portsmouth FC | - | Grimsby Town | 2:1 |
England