| 1. Round | 22/08/1959 | Chelsea FC | - | Preston North End | 4:4 | ||||
| 2. Round | 26/08/1959 | Manchester United | - | Chelsea FC | 0:1 | ||||
| 3. Round | 29/08/1959 | Leicester City | - | Chelsea FC | 3:1 | ||||
| 4. Round | 02/09/1959 | Chelsea FC | - | Manchester United | 3:6 | ||||
| 34. Round | 19/03/1960 | Chelsea FC | - | Blackpool FC | 2:3 |  |
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| 35. Round | 30/03/1960 | Blackburn Rovers | - | Chelsea FC | 1:0 | ||||
| 39. Round | 16/04/1960 | Chelsea FC | - | Nottingham Forest | 1:1 |
England