1. Round | 22/08/1959 | West Ham United | - | Leicester City | 3:0 | ||||
2. Round | 25/08/1959 | Preston North End | - | West Ham United | 1:1 | ||||
3. Round | 29/08/1959 | Burnley FC | - | West Ham United | 1:3 | ||||
4. Round | 31/08/1959 | West Ham United | - | Preston North End | 2:1 | ||||
5. Round | 05/09/1959 | West Ham United | - | Leeds United | 1:2 | ||||
6. Round | 09/09/1959 | Tottenham Hotspur | - | West Ham United | 2:2 | ||||
7. Round | 12/09/1959 | Bolton Wanderers | - | West Ham United | 5:1 | ||||
8. Round | 14/09/1959 | West Ham United | - | Tottenham Hotspur | 1:2 | ||||
9. Round | 19/09/1959 | Chelsea FC | - | West Ham United | 2:4 | ||||
10. Round | 26/09/1959 | West Ham United | - | West Bromwich Albion | 4:1 | ||||
11. Round | 03/10/1959 | Newcastle United | - | West Ham United | 0:0 | ||||
12. Round | 10/10/1959 | West Ham United | - | Luton Town | 3:1 | ||||
13. Round | 17/10/1959 | Everton FC | - | West Ham United | 0:1 | ||||
15. Round | 31/10/1959 | Fulham FC | - | West Ham United | 1:0 | ||||
26. Round | 16/01/1960 | Leeds United | - | West Ham United | 3:0 |