Cherundolo parlayed his success in the Bundesliga into a role with the United States national team. Cherundolo made his debut against Jamaica on September 8, 1999. Although he was on the roster for the 2002 FIFA World Cup (a late injury replacement for Chris Armas), Cherundolo himself was injured in training shortly before the event began and was unable to play. In the 2005 CONCACAF Gold Cup, Cherundolo sustained a knee injury from a tackle that prematurely ended his participation in the tournament. On March 22, 2006, Cherundolo played in a friendly match with the national team against Germany, whose roster included some teammates from Hannover 96. He scored his first international goal in the 4–1 loss.