At the 2008 Summer Olympics in Beijing, Massie qualified for his second U.S. squad, as a 26-year-old, in two track cycling events by receiving an automatic berth from the USA Cycling Team's Selection Camp. In the men's team sprint, held on the first day of the program, Massie helped his teammates Duvendeck and Michael Blatchford set an eighth-place time in 45.346 (an average speed of 59.542 km/h) on the morning prelims before losing out to the Brits (led by Olympic legend Chris Hoy) in the first round. The following day, in the men's keirin, Massie narrowly missed the second spot taken by the Netherlands' Theo Bos in his opening heat and finished fourth in the repechage against five other cyclists, thus eliminating him from the competition with a twenty-first place overall.