[3][4][5] As a youth, he played for the La Jolla Nomads club team, which won the California state championship six times with him.

Premier League side Bolton Wanderers agreed to a deal with Hannover for Cherundolo in 2005, but he declined, opting to remain in Germany.

[8] On March 19, 2014, Cherundolo announced his retirement from soccer citing failure to recover from a long-term knee injury as the main reason he left the game.

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.

[10] On June 12, 2006, for the first time, aged 27, Cherundolo made his debut in a FIFA World Cup match against the Czech Republic, playing in the first half for the U.S., who started the tournament with a 3–0 loss.

[11] Five days later, in the second match against Italy (who later won the tournament), Cherundolo played the full 90 minutes, helping the team to a 1–1 draw at Fritz-Walter-Stadion in Kaiserslautern.

In the first match of Group C against England, Cherundolo was in the starting lineup and played the full 90 minutes in a 1–1 draw at Royal Bafokeng Stadium.

[16] On June 18, he retained his position for the second match, playing in the entire game against Slovenia, which finished in a 2–2 draw, with the U.S. coming back from 2–0 down.

[17] In the 48th minute of the match, Cherundolo assisted Landon Donovan who beat Slovenian goalkeeper Samir Handanović with a powerful shot.

[32] Cherundolo married Mandy Rosier on New Year's Eve 2009 at the local St. Joseph Catholic parish church in the Hanover district of Vahrenwald-List.