| 1. Round | 28/08/1937 | Bolton Wanderers | - | Brentford FC | 2:0 |  |
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| 2. Round | 30/08/1937 | Blackpool FC | - | Bolton Wanderers | 2:2 | |
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| 3. Round | 04/09/1937 | Grimsby Town | - | Bolton Wanderers | 0:1 | ||||
| 4. Round | 06/09/1937 | Bolton Wanderers | - | Blackpool FC | 3:0 | ||||
| 5. Round | 11/09/1937 | Huddersfield Town | - | Bolton Wanderers | 1:0 | ||||
| 6. Round | 15/09/1937 | Bolton Wanderers | - | Arsenal FC | 1:0 | ||||
| 7. Round | 18/09/1937 | Bolton Wanderers | - | Everton FC | 1:2 | ||||
| 8. Round | 25/09/1937 | Wolverhampton Wanderers | - | Bolton Wanderers | 1:1 | ||||
| 9. Round | 02/10/1937 | Bolton Wanderers | - | Leicester City | 6:1 | |
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| 10. Round | 09/10/1937 | Sunderland AFC | - | Bolton Wanderers | 3:1 | ||||
| 12. Round | 23/10/1937 | Charlton Athletic | - | Bolton Wanderers | 1:1 | ||||
| 17. Round | 27/11/1937 | Bolton Wanderers | - | Birmingham FC | 1:1 | ||||
| 18. Round | 04/12/1937 | Portsmouth FC | - | Bolton Wanderers | 1:1 | ||||
| 19. Round | 11/12/1937 | Bolton Wanderers | - | Liverpool FC | 0:0 | ||||
| 20. Round | 18/12/1937 | Middlesbrough FC | - | Bolton Wanderers | 1:2 | |
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| 28. Round | 12/02/1938 | Leicester City | - | Bolton Wanderers | 1:1 | ||||
| 29. Round | 19/02/1938 | Bolton Wanderers | - | Sunderland AFC | 1:1 | |
England