Whitfield won the gold medal in the men's triathlon at the 2000 Olympic Games in Sydney. It was the first time triathlon was included on the Olympic program. Whitfield then went on to win a gold medal at the 2002 Commonwealth Games in Manchester and a silver medal at the 2008 Olympic Games in Beijing.
At the 2012 Olympic Games in London, Whitfield was the flag bearer for team Canada during the Opening Ceremonies.
Whitfield now plans to work as a consultant for Fantan Group, an event management and creative industry company, and will be based in Victoria. The company is forming a new sports entertainment division in western British Columbia.
There has been some speculation that Whitfield will continue with various ironmans, but at this time it is uncertain if Whitfield will go that particular route.