| 1. Round | 27/08/1927 | Derby County | - | West Ham United | 2:3 | ||||
| 2. Round | 01/09/1927 | West Ham United | - | Sunderland AFC | 2:4 | ||||
| 3. Round | 03/09/1927 | West Ham United | - | Huddersfield Town | 4:2 | ||||
| 5. Round | 10/09/1927 | West Ham United | - | Portsmouth FC | 4:2 | ||||
| 6. Round | 17/09/1927 | Leicester City | - | West Ham United | 2:3 | ||||
| 7. Round | 24/09/1927 | West Ham United | - | Liverpool FC | 3:1 | ||||
| 8. Round | 01/10/1927 | Arsenal FC | - | West Ham United | 2:2 | ||||
| 9. Round | 08/10/1927 | West Ham United | - | Burnley FC | 2:0 | ||||
| 10. Round | 15/10/1927 | Bury FC | - | West Ham United | 3:1 | ||||
| 11. Round | 22/10/1927 | Everton FC | - | West Ham United | 7:0 | ||||
| 12. Round | 29/10/1927 | West Ham United | - | Manchester United | 1:2 | ||||
| 13. Round | 05/11/1927 | Tottenham Hotspur | - | West Ham United | 5:3 |
England