| 1. Journée | 27.08.1938 | Bolton Wanderers | - | Charlton Athletic | 2:1 |  |
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| 2. Journée | 31.08.1938 | Manchester United | - | Bolton Wanderers | 2:2 | ||||
| 3. Journée | 03.09.1938 | Portsmouth FC | - | Bolton Wanderers | 2:1 | ||||
| 4. Journée | 05.09.1938 | Bolton Wanderers | - | Chelsea FC | 0:2 | ||||
| 27. Journée | 04.02.1939 | Middlesbrough FC | - | Bolton Wanderers | 1:2 |
Écosse