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Chelsea matches where Billy Holmes was opposition manager/coach
| Date | Venue | Opponent | Score | Comp |
| 20/04/1907 | Millfields Road | Clapton Orient | 1-0 | Football League Division 2 |
| 08/10/1910 | Millfields Road | Clapton Orient | 0-0 | Football League Division 2 |
| 11/02/1911 | Stamford Bridge | Clapton Orient | 1-0 | Football League Division 2 |
| 28/10/1911 | Millfields Road | Clapton Orient | 4-1 | Football League Division 2 |
| 02/03/1912 | Stamford Bridge | Clapton Orient | 3-0 | Football League Division 2 |