1. Round | 22/08/1959 | Blackpool FC | - | Bolton Wanderers | 3:2 | ||||
2. Round | 26/08/1959 | Bolton Wanderers | - | Blackburn Rovers | 0:3 | ||||
3. Round | 29/08/1959 | Bolton Wanderers | - | Everton FC | 2:1 | ||||
4. Round | 31/08/1959 | Blackburn Rovers | - | Bolton Wanderers | 1:0 | ||||
5. Round | 05/09/1959 | Luton Town | - | Bolton Wanderers | 0:0 | ||||
6. Round | 09/09/1959 | Bolton Wanderers | - | Arsenal FC | 0:1 | ||||
7. Round | 12/09/1959 | Bolton Wanderers | - | West Ham United | 5:1 | ||||
8. Round | 15/09/1959 | Arsenal FC | - | Bolton Wanderers | 2:1 | ||||
9. Round | 19/09/1959 | Bolton Wanderers | - | Fulham FC | 3:2 | ||||
10. Round | 26/09/1959 | Nottingham Forest | - | Bolton Wanderers | 2:0 | ||||
11. Round | 03/10/1959 | Bolton Wanderers | - | Sheffield Wednesday | 1:0 | ||||
12. Round | 10/10/1959 | Chelsea FC | - | Bolton Wanderers | 0:2 | ||||
13. Round | 17/10/1959 | Bolton Wanderers | - | West Bromwich Albion | 0:0 | ||||
14. Round | 24/10/1959 | Newcastle United | - | Bolton Wanderers | 0:2 | ||||
15. Round | 31/10/1959 | Bolton Wanderers | - | Leeds United | 1:1 | ||||
16. Round | 07/11/1959 | Tottenham Hotspur | - | Bolton Wanderers | 0:2 | ||||
17. Round | 14/11/1959 | Bolton Wanderers | - | Manchester United | 1:1 |