In the first year of competition, he became one of the club's and leagues first premiership players, during the 1897 VFL season, under the captaincy of George Stuckey.
Waugh made his debut against Geelong in Round 1 of the season, at Corio Oval.
[1] His 23 goals was the third-highest in the League, behind Jack Leith of Melbourne (26), and Eddy James of Geelong (27).
[2] He was the youngest son of Dr James S. Waugh, the first president of Wesley College.
After retiring from football, he entered the insurance industry and became the chief executive officer of the National Mutual Company in South Africa.