1898–99 Southern Football League

The 1898–99 season was the fifth in the history of the Southern League. This season saw the expansion of Division One up to 14 teams and creation of Division Two South-West, though it was disbanded at the end of the season after all its clubs left. No Southern League clubs applied for promotion to the Football League. Southampton were Division One champions for the third season in a row. Overall Division Two champions being decided in a playoff in which Thames Ironworks defeated Cowes 3-1 at The Den.