| 16/9/1899 |
|
Friendly |
Croydon Adults |
1 - 2 |
| 23/9/1899 |
|
Friendly |
Wingfield House |
2 - 2 |
| 30/9/1899 |
|
Friendly |
Dulwich Hamlet |
0 - 5 |
| 7/10/1899 |
|
Friendly |
St. Saviour's Elmhurst |
1 - 1 |
| 14/10/1899 |
|
Clapham League |
Celtic Rangers |
1 - 1 |
| 28/10/1899 |
|
London Junior Cup (2nd Round) |
Mottingham |
2 - 0 |
| 4/11/1899 |
|
Clapham League |
Southfields St. Barnabus |
1 - 0 |
| 11/11/1899 |
|
Clapham League |
Merton Manor *Match abandoned |
0 - 1* |
| 18/11/1899 |
|
London Junior Cup (3rd Round) |
Peckham Albion |
6 - 2 |
| 25/11/1899 |
|
Clapham League |
Tooting Graveney |
0 - 3 |
| 2/12/1899 |
|
London Junior Cup (4th Round) |
West Norwood Albion |
1 - 0 |
| 9/12/1899 |
|
Clapham League |
Wingfield House |
3 - 0 |
| 16/12/1899 |
|
South Western Cup (2nd Round) |
East Hill Endeavour |
3 - 2 |
| 25/12/1899 |
|
Friendly |
Westminster |
10 - 0 |
| 26/12/1899 |
|
Friendly |
Holy Trinity Canning Town |
4 - 0 |
| 30/12/1899 |
|
Clapham League |
Wandsworth 'A' |
4 - 0 |
| 6/1/1900 |
|
London Junior Cup (Semi-Final) |
Croydon Wanderers |
1 - 0 |
| 13/1/1900 |
|
London Junior Cup (Final) |
Dulwich Hamlet |
1 - 3 |
| 20/1/1900 |
|
Clapham League |
St. Saviour's Elmhurst |
0 - 3 |
| 27/1/1900 |
|
South Western Cup (3rd Round) |
Wingfield House |
0 - 2 |
| 10/2/1900 |
|
Clapham League |
Battersea St. John's |
5 - 0 |
| 24/2/1900 |
|
Clapham League |
Celtic Rangers |
0 - 2 |
| 3/3/1900 |
|
Friendly |
North Dulwich |
5 - 0 |
| 10/3/1900 |
|
Friendly |
Rye House |
4 - 0 |
| 17/3/1900 |
|
Clapham League |
Battersea St. John's |
7 - 0 |
| 24/3/1900 |
|
Clapham League |
St. Saviour's Elmhurst |
1 - 2 |
| 31/3/1900 |
|
Clapham League |
Merton Manor |
1 - 2 |
| 7/4/1900 |
|
Clapham League |
Tooting Graveney |
0 - 3 |
| 14/4/1900 |
|
Friendly |
Chesham Generals |
3 - 5 |
| 16/4/1900 |
|
Friendly |
Aylesbury United |
1 - 4 |
| 28/4/1900 |
|
Clapham League |
Merton Manor |
4 - 1 |