| 5. Round | 10/09/1938 | Leeds United | - | Bolton Wanderers | 1:2 | ||||
| 6. Round | 17/09/1938 | Bolton Wanderers | - | Liverpool FC | 3:1 |  |
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| 7. Round | 24/09/1938 | Leicester City | - | Bolton Wanderers | 0:0 | ||||
| 8. Round | 01/10/1938 | Bolton Wanderers | - | Middlesbrough FC | 4:1 | |
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| 9. Round | 08/10/1938 | Birmingham FC | - | Bolton Wanderers | 0:2 | ||||
| 10. Round | 15/10/1938 | Bolton Wanderers | - | Everton FC | 4:2 | |
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| 11. Round | 22/10/1938 | Huddersfield Town | - | Bolton Wanderers | 2:1 | |
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| 12. Round | 29/10/1938 | Bolton Wanderers | - | Arsenal FC | 1:1 | ||||
| 13. Round | 05/11/1938 | Brentford FC | - | Bolton Wanderers | 2:2 | ||||
| 14. Round | 12/11/1938 | Bolton Wanderers | - | Blackpool FC | 0:1 | ||||
| 15. Round | 19/11/1938 | Derby County | - | Bolton Wanderers | 3:0 | ||||
| 17. Round | 03/12/1938 | Sunderland AFC | - | Bolton Wanderers | 2:2 | ||||
| 19. Round | 17/12/1938 | Wolverhampton Wanderers | - | Bolton Wanderers | 1:1 | ||||
| 20. Round | 24/12/1938 | Charlton Athletic | - | Bolton Wanderers | 2:1 | ||||
| 22. Round | 27/12/1938 | Preston North End | - | Bolton Wanderers | 2:2 | |
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| 23. Round | 31/12/1938 | Bolton Wanderers | - | Portsmouth FC | 5:1 | |
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| 36. Round | 02/01/1939 | Bolton Wanderers | - | Stoke City | 1:3 | |
Wales