| 1. Round | 20/08/1960 | Bolton Wanderers | - | Birmingham City | 2:2 |  |
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| 2. Round | 24/08/1960 | Bolton Wanderers | - | Wolverhampton Wanderers | 0:2 | ||||
| 3. Round | 27/08/1960 | West Ham United | - | Bolton Wanderers | 2:1 | ||||
| 4. Round | 31/08/1960 | Wolverhampton Wanderers | - | Bolton Wanderers | 3:1 | ||||
| 5. Round | 03/09/1960 | Bolton Wanderers | - | Chelsea FC | 4:1 | ||||
| 6. Round | 07/09/1960 | Bolton Wanderers | - | Tottenham Hotspur | 1:2 | ||||
| 7. Round | 10/09/1960 | Blackpool FC | - | Bolton Wanderers | 0:1 | ||||
| 8. Round | 14/09/1960 | Tottenham Hotspur | - | Bolton Wanderers | 3:1 | ||||
| 9. Round | 17/09/1960 | Bolton Wanderers | - | Everton FC | 3:4 | |
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| 10. Round | 24/09/1960 | Blackburn Rovers | - | Bolton Wanderers | 3:1 | ||||
| 11. Round | 01/10/1960 | Bolton Wanderers | - | Manchester United | 1:1 | ||||
| 12. Round | 08/10/1960 | Bolton Wanderers | - | West Bromwich Albion | 0:1 |
England