Waugh's career as a rugby player began at the Shore school, playing in the First XV in his final 3 years and captaining the team in 1997.

[citation needed] His professional career began in 1999, playing for the Waratahs, and later that year gained selection for the Wallabies Spring tour of the UK and Europe, making his test debut as a replacement in the match against England.

Waugh continued receiving game time with the team until early 2002 when an ankle injury caused him to miss out on the international season.

After his recovery, Waugh returned to the field to be named vice-captain of the 2003 Rugby World Cup team, who were ultimately runners-up.

In December 2013, Waugh was a crew member aboard racing supermaxi yacht Perpetual Loyal in the 2013 Sydney to Hobart Yacht Race, with his other celebrity crew members, Karl Stefanovic, Larry Emdur, Tom Slingsby, Jude Bolton and Guillaume Brahimi.