Clegg was recruited from the South Melbourne Under 19's after winning the 1944 Melbourne Boys Football League's best and fairest award[1] and was best on ground in the 1944 grand final for South Melbourne.[2]
Richmond were very keen to secure Clegg's signature in 1944, before he settled on South Melbourne.[3][4][5]
Clegg debuted in 1945 and from early on South Melbourne knew they had a star in the making[6] and he played in South Melbourne's losing 1945 VFL grand final.[7]
By the time Clegg was 18 years old he had established himself as a gifted senior player in the VFL in 1946.[8]
A brilliant key position player at either centre half-forward or centre half-back, he was awarded the Brownlow Medal in 1949[9] while playing with the then South Melbourne Football Club and was runner up in the Brownlow in 1951.[10]
Clegg sought a clearance to New Norfolk in early 1951 and was refused a clearance,[16] then was later appointed as vice captain of South Melbourne FC in 1951.[17] Clegg won the 1951 London Stores Best Player Award in the VFL.[18]
In 1951, Clegg took an incredible 32 marks against Fitzroy at the Lakeside Oval.[19]
Clegg was appointed as club captain in 1953 and also lead the club in 1954 too.[20]
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.[24]