| Date | Competition | Opponents | Venue | Score | Goalscorers | Att | Rep | Vid |
|---|---|---|---|---|---|---|---|---|
| 16/09/1899 | SLge D1 | Queens Park Rangers | A | 0-2 | 6300 |  | ||
| 23/09/1899 | SLge D1 | CHATHAM | H | 1-1 | Seeley | 5000 |  | |
| 30/09/1899 | SLge D1 | Reading | A | 1-3 | Pangbourne | 2500 |  | |
| 07/10/1899 | SLge D1 | SHEPPEY UTD | H | 2-2 | Graham,Innes | 3000 |  | |
| 14/10/1899 | SLge D1 | Bristol Rovers | A | 1-0 | Seeley | 3000 |  | |
| 28/10/1899 | FACQ3 | Woolwich Arsenal | A | 1-1 | Swan | 5500 |  | |
| 01/11/1899 | FACQ3R | WOOLWICH ARSENAL | H | 0-0 | 2500 |  | ||
| 06/11/1899 | FACQ3R2 | Woolwich Arsenal | Millwall | 2-2 (aet) | Pangbourne(2) | 3000 |  | |
| 08/11/1899 | FACQ3R3 | Woolwich Arsenal | Tottenham | 1-1 | MacDonald | 2000 |  | |
| 02/12/1899 | SLge D1 | Gravesend Utd | A | 0-2 | 2000 |  |