[7][8] Leopold first appeared in historical records in 1898, competing in the Metropolitan Junior Football Association (MJFA).

[7] At the time, the club played its home games at Warehousemen's Cricket Ground.

[9] As South Melbourne was a seniors side, Leopold operated as its juniors team.

[13] A fifth premiership was won in 1915, before the impacts of World War I in Australia affected football competitions.

The VFL introduced a reserves competition in 1919, known as the Victorian Junior Football League (VJFL), and Leopold contested as South Melbourne's affiliate until the end of the 1924 season.