| 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 | | |
| 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 | | |
| 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 | | |
| 03/02/1900 | SLge D1 | READING | H | 4-2 | Frettingham(2),Pangbourne(2) | 500 | | |
| 10/02/1900 | SLge D1 | Sheppey Utd | A | 2-2 | Pangbourne,OG | 1000 | | |
| 24/02/1900 | SLge D1 | Bedminster | A | 1-3 | Swan | 1000 | | |
| 03/03/1900 | SLge D1 | BRISTOL ROVERS | H | 2-0 | Innes(p),Frettingham | 1800 | | |
| 10/03/1900 | SLge D1 | Portsmouth | A | 1-5 | Frettingham | 5000 | | |
| 17/03/1900 | SLge D1 | THAMES IRONWORKS | H | 3-1 | Frettingham(2),Pangbourne | 1000 | | |
| 24/03/1900 | SLge D1 | Tottenham | A | 0-1 | | 5000 | | |
| 07/04/1900 | SLge D1 | GRAVESEND UTD | H | 0-1 | | 1500 | | |
| 14/04/1900 | SLge D1 | Swindon Town | A | 1-1 | Frettingham | 2000 | | |
| 21/04/1900 | SLge D1 | BRISTOL CITY | H | 1-0 | Swan | 1200 | | |
| 28/04/1900 | SLge D1 | TOTTENHAM | H | 1-2 | Gladwell | 3000 | | |
| | Bad Language | | | | | | |
| | Thames and Medway Combination Champions | | | | | | |
