| 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 | ||||
| 8. Round | 01/10/1938 | Chelsea FC | - | Stoke City | 1:1 | ||||
| 9. Round | 08/10/1938 | Blackpool FC | - | Chelsea FC | 5:1 | ||||
| 17. Round | 03/12/1938 | Everton FC | - | Chelsea FC | 4:1 | ||||
| 31. Round | 08/03/1939 | Derby County | - | Chelsea FC | 0:1 | ||||
| 38. Round | 10/04/1939 | Chelsea FC | - | Charlton Athletic | 1:3 |
England