| 19. Round | 17/12/1938 | Portsmouth FC | - | Chelsea FC | 2:1 | ||||
| 20. Round | 24/12/1938 | Chelsea FC | - | Liverpool FC | 4:1 | ||||
| 21. Round | 26/12/1938 | Leeds United | - | Chelsea FC | 1:1 | ||||
| 22. Round | 27/12/1938 | Chelsea FC | - | Leeds United | 2:2 | ||||
| 23. Round | 31/12/1938 | Leicester City | - | Chelsea FC | 3:2 | ||||
| 24. Round | 14/01/1939 | Chelsea FC | - | Middlesbrough FC | 4:2 | ||||
| 26. Round | 28/01/1939 | Chelsea FC | - | Manchester United | 0:1 | ||||
| 27. Round | 04/02/1939 | Stoke City | - | Chelsea FC | 6:1 | ||||
| 30. Round | 25/02/1939 | Chelsea FC | - | Brentford FC | 1:3 | ||||
| 39. Round | 15/04/1939 | Huddersfield Town | - | Chelsea FC | 3:1 | ||||
| 40. Round | 22/04/1939 | Chelsea FC | - | Portsmouth FC | 1:0 | ||||
| 25. Round | 26/04/1939 | Birmingham FC | - | Chelsea FC | 1:1 | ||||
| 41. Round | 29/04/1939 | Preston North End | - | Chelsea FC | 1:1 | ||||
| 42. Round | 06/05/1939 | Chelsea FC | - | Bolton Wanderers | 1:1 |
Scotland