1. Round | 09/08/1969 | Liverpool FC | - | Chelsea FC | 4:1 | ||||
3. Round | 16/08/1969 | Chelsea FC | - | Ipswich Town | 1:0 | ||||
4. Round | 20/08/1969 | Chelsea FC | - | West Ham United | 0:0 | ||||
5. Round | 23/08/1969 | Southampton FC | - | Chelsea FC | 2:2 | ||||
6. Round | 27/08/1969 | Tottenham Hotspur | - | Chelsea FC | 1:1 | ||||
11. Round | 20/09/1969 | Leeds United | - | Chelsea FC | 2:0 |