| Date | Competition | Opponents | Venue | Score | Goalscorers | Att | Rep | Vid |
|---|---|---|---|---|---|---|---|---|
| 28/10/1899 | FACQ3 | Woolwich Arsenal | A | 1-1 | Swan | 5500 |  | |
| 06/11/1899 | FACQ3R2 | Woolwich Arsenal | Millwall | 2-2 (aet) | Pangbourne(2) | 3000 |  | |
| 08/11/1899 | FACQ3R3 | Woolwich Arsenal | Tottenham | 1-1 | MacDonald | 2000 |  | |
| 14/11/1899 | FACQ3R4 | Woolwich Arsenal | Gravesend | 1-0 | Atherton | 3500 |  |