5. Round | 05/09/1959 | Arsenal FC | - | Tottenham Hotspur | 1:1 | ||||
6. Round | 09/09/1959 | Tottenham Hotspur | - | West Ham United | 2:2 | ||||
8. Round | 14/09/1959 | West Ham United | - | Tottenham Hotspur | 1:2 | ||||
11. Round | 03/10/1959 | Tottenham Hotspur | - | Burnley FC | 1:1 | ||||
16. Round | 07/11/1959 | Tottenham Hotspur | - | Bolton Wanderers | 0:2 | ||||
17. Round | 14/11/1959 | Luton Town | - | Tottenham Hotspur | 1:0 | ||||
18. Round | 21/11/1959 | Tottenham Hotspur | - | Everton FC | 3:0 | ||||
29. Round | 13/02/1960 | Tottenham Hotspur | - | Leicester City | 1:2 | ||||
35. Round | 26/03/1960 | Bolton Wanderers | - | Tottenham Hotspur | 2:1 | ||||
36. Round | 02/04/1960 | Tottenham Hotspur | - | Luton Town | 1:1 | ||||
37. Round | 09/04/1960 | Everton FC | - | Tottenham Hotspur | 2:1 | ||||
40. Round | 18/04/1960 | Tottenham Hotspur | - | Chelsea FC | 0:1 | ||||
41. Round | 23/04/1960 | Wolverhampton Wanderers | - | Tottenham Hotspur | 1:3 | ||||
42. Round | 30/04/1960 | Tottenham Hotspur | - | Blackpool FC | 4:1 |