1. Round | 27/08/1938 | Liverpool FC | - | Chelsea FC | 2:1 | ||||
2. Round | 31/08/1938 | Chelsea FC | - | Preston North End | 3:1 | ||||
3. Round | 03/09/1938 | Chelsea FC | - | Leicester City | 3:0 | ||||
4. Round | 05/09/1938 | Bolton Wanderers | - | Chelsea FC | 0:2 | ||||
5. Round | 10/09/1938 | Middlesbrough FC | - | Chelsea FC | 1:1 | ||||
6. Round | 17/09/1938 | Chelsea FC | - | Birmingham FC | 2:2 | ||||
7. Round | 24/09/1938 | Manchester United | - | Chelsea FC | 5:1 | ||||
11. Round | 22/10/1938 | Brentford FC | - | Chelsea FC | 1:0 | ||||
23. Round | 31/12/1938 | Leicester City | - | Chelsea FC | 3:2 |