| Date | Competition | Opponents | Venue | Score | Goalscorers | Att | Rep | Vid |
|---|---|---|---|---|---|---|---|---|
| 02/09/1899 | SLge D1 | Southampton | A | 2-6 | Frettingham,MacDonald | 3000 |  | |
| 09/09/1899 | SLge D1 | MILLWALL ATHLETIC | H | 1-1 | MacDonald | 4000 |  | |
| 16/09/1899 | SLge D1 | Queens Park Rangers | A | 0-2 | 6300 |  | ||
| 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 |  | ||
| 04/11/1899 | SLge D1 | PORTSMOUTH | H | 1-0 | Frettingham | 1500 |  | |
| 06/11/1899 | FACQ3R2 | Woolwich Arsenal | Millwall | 2-2 (aet) | Pangbourne(2) | 3000 |  | |
| 08/11/1899 | FACQ3R3 | Woolwich Arsenal | Tottenham | 1-1 | MacDonald | 2000 |  | |
| 11/11/1899 | SLge D1 | Thames Ironworks | A | 0-0 | 3000 |  | ||
| 14/11/1899 | FACQ3R4 | Woolwich Arsenal | Gravesend | 1-0 | Atherton | 3500 |  | |
| 18/11/1899 | FACQ4 | THAMES IRONWORKS | H | 0-0 | 3000 |  | ||
| 23/11/1899 | FACQ4R | Thames Ironworks | A | 0-2 | 2000 |  | ||
| 02/12/1899 | SLge D1 | Gravesend Utd | A | 0-2 | 2000 |  | ||
| 09/12/1899 | SLge D1 | SWINDON TOWN | H | 4-2 | MacDonald(2),Swan,Pangbourne | 2000 |  | |
| 16/12/1899 | SLge D1 | Bristol City | A | 1-2 | Frettingham | 3500 |  | |
| 18/12/1899 | SLge D1 | BEDMINSTER | H | 5-0 | Swan(2),MacDonald,Frettingham,T.Gray | 1500 |  | |
| 30/12/1899 | SLge D1 | SOUTHAMPTON | H | 1-2 | Swan | 2500 |  | |
| 06/01/1900 | SLge D1 | Millwall Athletic | A | 1-4 | MacDonald | 3000 |  | |
| 13/01/1900 | SLge D1 | QUEENS PARK RANGERS | H | 0-3 | 2000 |  | ||
| 20/01/1900 | SLge D1 | Chatham | A | 2-1 | T.Gray,Hutcheson | 3500 |  |