1. Round | 27/08/1938 | Arsenal FC | - | Portsmouth FC | 2:0 | ||||
4. Round | 31/08/1938 | Portsmouth FC | - | Blackpool FC | 1:0 | ||||
3. Round | 03/09/1938 | Portsmouth FC | - | Bolton Wanderers | 2:1 | ||||
2. Round | 06/09/1938 | Grimsby Town | - | Portsmouth FC | 2:1 | ||||
5. Round | 10/09/1938 | Portsmouth FC | - | Huddersfield Town | 4:0 | ||||
6. Round | 17/09/1938 | Everton FC | - | Portsmouth FC | 5:1 | ||||
7. Round | 24/09/1938 | Portsmouth FC | - | Wolverhampton Wanderers | 1:0 | ||||
8. Round | 01/10/1938 | Aston Villa | - | Portsmouth FC | 2:0 | ||||
9. Round | 08/10/1938 | Portsmouth FC | - | Sunderland AFC | 2:1 | ||||
10. Round | 15/10/1938 | Preston North End | - | Portsmouth FC | 2:2 | ||||
11. Round | 22/10/1938 | Portsmouth FC | - | Charlton Athletic | 0:2 | ||||
12. Round | 29/10/1938 | Leeds United | - | Portsmouth FC | 2:2 | ||||
15. Round | 19/11/1938 | Portsmouth FC | - | Middlesbrough FC | 1:1 | ||||
16. Round | 26/11/1938 | Birmingham FC | - | Portsmouth FC | 2:0 | ||||
17. Round | 03/12/1938 | Portsmouth FC | - | Manchester United | 0:0 | ||||
27. Round | 04/02/1939 | Portsmouth FC | - | Aston Villa | 0:0 |