Whitfield, who had joint Canadian-Australian citizenship, was not one of the favourites at the Olympic Games. He was ranked thirteenth in the world and had not won a triathlon in a year. But while training at the Olympic Village, he was amazed at how fit he felt. Conrad Stoltz of South Africa and world champion Olivier Marceau of France broke away from the field during the fifth of six bike laps and opened up a lead of almost a minute. On that same lap, a 15-man crash occurred and Whitfield was forced to put his foot down and skid to a stop.
He began the 10km run in 24th place. Stoltz faded while Marceau held on for six kilometres, before being passed by Stephan Vuckovic of Germany. Whitfield, who had gradually moved his way up through the field, caught Vuckovic, but with 1'000m to go, the German opened up a lead of almost 25m. Whitfield cut the gap in half and then began his final sprint with 450m left. He passed Vuckovic about 200m from the finish line and won easily. At the Athens Olympic Games in 2004, Simon Whitfield finished in 11th place. Four years later, he participated at the 2008 Olympic Games in Beijing, where he won a silver medal.