|The Pirate revisited||
Sheppy United, 9-September-1899
Chatham United, 13-October-1899.
Thames Ironworks, 14-October-1899. (Postponed due to Thame's cup commitments).
New Brompton, 14-October-1899.
Eastleigh, 28-October,1899, F.A.Cup, 3rd Qual Round.
Swindon Town, 11-November-1899.
Portsmouth, 18-November-1899, F.A.Cup, 4th Qual Round.
Brighton United, 13-January-1900,
Thames Ironworks, 15-January-1900.
Tottenham Hotspur, 24-February-1900.
Gravesend United, 10-March-1900. (No match, Gravesend did not turn up).
Bristol City, 2-April-1900, G.C.S.F.
Bristol City, 13-April-1900.
Gravesend United, 18-April-1900.
Bristol City, 6-September-1899, Friendly.
Brighton United, 16-September-1899.
Tottenham Hotspur, 21-October-1899, Abandoned 55 Mins, due to fog.
Gravesend United, 4-November-1899.
Portsmouth, 22-November-1899, F.A.Cup, 4th Qual Round.
Sheppy United, 9-December-1899.
Bristol City, 26-December-1899.
Bristol City, 6-January-1900, Friendly.
Thames Ironworks, 17-February-1900.
New Brompton, 3-March-1900.
Swindon Town, 17-March-1900.
Tottenham Hotspur, 19-March-1900.
Bristol City, 9-April-1900, G.C.S.F. Replay.