| 1. Round | 27/08/1938 | Bolton Wanderers | - | Charlton Athletic | 2:1 | ||||
| 2. Round | 31/08/1938 | Manchester United | - | Bolton Wanderers | 2:2 | ||||
| 3. Round | 03/09/1938 | Portsmouth FC | - | Bolton Wanderers | 2:1 | ||||
| 4. Round | 05/09/1938 | Bolton Wanderers | - | Chelsea FC | 0:2 | ||||
| 5. Round | 10/09/1938 | Leeds United | - | Bolton Wanderers | 1:2 | ||||
| 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 | ||||
| 16. Round | 26/11/1938 | Bolton Wanderers | - | Grimsby Town | 1:1 | ||||
| 17. Round | 03/12/1938 | Sunderland AFC | - | Bolton Wanderers | 2:2 | ||||
| 18. Round | 10/12/1938 | Bolton Wanderers | - | Aston Villa | 1:2 |
England