1. Round | 20/08/1949 | Birmingham City | - | Chelsea FC | 0:3 | ||||
2. Round | 24/08/1949 | Chelsea FC | - | Arsenal FC | 1:2 | ||||
3. Round | 27/08/1949 | Chelsea FC | - | Derby County | 1:2 | ||||
4. Round | 31/08/1949 | Arsenal FC | - | Chelsea FC | 2:3 | ||||
5. Round | 03/09/1949 | West Bromwich Albion | - | Chelsea FC | 1:1 | ||||
9. Round | 17/09/1949 | Fulham FC | - | Chelsea FC | 1:1 | ||||
10. Round | 24/09/1949 | Stoke City | - | Chelsea FC | 2:3 | ||||
11. Round | 01/10/1949 | Chelsea FC | - | Burnley FC | 0:1 | ||||
12. Round | 08/10/1949 | Chelsea FC | - | Manchester City | 3:0 | ||||
13. Round | 15/10/1949 | Charlton Athletic | - | Chelsea FC | 1:0 | ||||
14. Round | 22/10/1949 | Chelsea FC | - | Aston Villa | 1:3 | ||||
16. Round | 05/11/1949 | Chelsea FC | - | Portsmouth FC | 1:4 | ||||
39. Round | 10/04/1950 | Bolton Wanderers | - | Chelsea FC | 1:0 | ||||
40. Round | 15/04/1950 | Chelsea FC | - | Wolverhampton Wanderers | 0:0 |