Whitfield was named to the 2008 Summer Olympics team and won a silver medal while competing at his third consecutive games. With a time of 1:48:58, he finished 5 seconds behind the German gold medalist. Whitfield's accomplishment was made even more impressive considering he was a distant fourth behind the lead three runners heading into the final kilometre of the run before he burst forth into the lead with 200 metres remaining. Whitfield, exhausted by his effort to get back into the lead, was then passed by the eventual winner Jan Frodeno of Germany at the end of the race.