| 24. Round | 14/01/1939 | Bolton Wanderers | - | Leeds United | 2:2 | ||||
| 25. Round | 25/01/1939 | Liverpool FC | - | Bolton Wanderers | 1:2 |  |
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| 26. Round | 28/01/1939 | Bolton Wanderers | - | Leicester City | 4:0 | |
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| 27. Round | 04/02/1939 | Middlesbrough FC | - | Bolton Wanderers | 1:2 | |
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| 29. Round | 18/02/1939 | Everton FC | - | Bolton Wanderers | 2:1 | ||||
| 28. Round | 22/02/1939 | Bolton Wanderers | - | Birmingham FC | 3:0 | ||||
| 39. Round | 15/04/1939 | Aston Villa | - | Bolton Wanderers | 1:3 | |
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| 40. Round | 22/04/1939 | Bolton Wanderers | - | Wolverhampton Wanderers | 0:0 | ||||
| 21. Round | 26/04/1939 | Bolton Wanderers | - | Preston North End | 0:2 | ||||
| 41. Round | 29/04/1939 | Bolton Wanderers | - | Manchester United | 0:0 |
Scotland