2. Round | 24/08/1949 | Chelsea FC | - | Arsenal FC | 1:2 | ||||
3. Round | 27/08/1949 | Chelsea FC | - | Derby County | 1:2 | ||||
17. Round | 12/11/1949 | Huddersfield Town | - | Chelsea FC | 1:2 | ||||
18. Round | 19/11/1949 | Chelsea FC | - | Everton FC | 3:2 | ||||
32. Round | 08/03/1950 | Chelsea FC | - | Charlton Athletic | 1:3 | ||||
33. Round | 11/03/1950 | Everton FC | - | Chelsea FC | 1:1 |