| 1. Round | 30/08/1930 | Grimsby Town | - | Chelsea FC | 0:1 | ||||
| 2. Round | 03/09/1930 | Newcastle United | - | Chelsea FC | 1:0 | ||||
| 3. Round | 06/09/1930 | Chelsea FC | - | Manchester United | 6:2 | ||||
| 4. Round | 08/09/1930 | Sheffield Wednesday | - | Chelsea FC | 1:1 | ||||
| 5. Round | 13/09/1930 | West Ham United | - | Chelsea FC | 4:1 | ||||
| 6. Round | 15/09/1930 | Chelsea FC | - | Sheffield Wednesday | 0:0 | ||||
| 7. Round | 20/09/1930 | Chelsea FC | - | Bolton Wanderers | 0:1 | ||||
| 8. Round | 27/09/1930 | Liverpool FC | - | Chelsea FC | 3:1 | ||||
| 18. Round | 06/12/1930 | Derby County | - | Chelsea FC | 6:2 | ||||
| 19. Round | 13/12/1930 | Chelsea FC | - | Sunderland AFC | 5:0 | ||||
| 20. Round | 20/12/1930 | Portsmouth FC | - | Chelsea FC | 1:1 |
Scotland