| 2. Round | 05/09/1914 | Tottenham Hotspur | - | Chelsea FC | 1:1 | ||||
| 3. Round | 09/09/1914 | Bradford City | - | Chelsea FC | 2:2 | ||||
| 6. Round | 26/09/1914 | Chelsea FC | - | Sheffield United | 1:1 | ||||
| 9. Round | 17/10/1914 | Bradford Park Avenue | - | Chelsea FC | 3:0 | ||||
| 10. Round | 24/10/1914 | Chelsea FC | - | Oldham Athletic | 2:2 | ||||
| 11. Round | 31/10/1914 | Manchester United | - | Chelsea FC | 2:2 | ||||
| 12. Round | 07/11/1914 | Chelsea FC | - | Bolton Wanderers | 2:1 | ||||
| 13. Round | 14/11/1914 | Blackburn Rovers | - | Chelsea FC | 3:2 | ||||
| 14. Round | 21/11/1914 | Chelsea FC | - | Notts County | 4:1 | ||||
| 15. Round | 28/11/1914 | Sunderland AFC | - | Chelsea FC | 2:1 | ||||
| 16. Round | 05/12/1914 | Chelsea FC | - | The Wednesday FC | 0:0 |
England