[2] Richmond were very keen to secure Clegg's signature in 1944, before he settled on South Melbourne.

[7] By the time Clegg was 18 years old he had established himself as a gifted senior player in the VFL in 1946.

Clegg played 42 first eleven games of Victorian Premier Cricket for South Melbourne between 1942 and 1947[23] before giving it away to concentrate on VFL football.

Clegg made his debut in round one, 1942 as a 14 year old left hand bat.

[25] In 2003, Clegg was named at centre half back in South Melbourne's Team of the Century.