On May 28, 2005, he scored his first international goal on his sixth cap, a consolation in a 2–1 defeat to England at Soldier Field, Chicago, by heading in after a save by goalkeeper David James. Dempsey's first international tournament was the United States' victorious 2005 CONCACAF Gold Cup campaign; he netted their first goal, equalising as they came from behind to defeat Cuba 4–1 at Qwest Field in Seattle.