Olsen at one time seemed like the right midfielder of the future for the U.S. national team, as he received his first cap soon after his Rookie of the Year season, on November 6, 1998 against Australia, and he was a significant player for the team in the 1999 season. He scored his first international goal during his first international start, which was against Chile on February 21, 1999. As the youngest player on the team. He received a cross from Brian McBride during the 58th minute. He then hit a side volley past goalie Marcelo Ramirez into the left corner of the goal. In 1999, he earned the U.S. Soccer Young Male Athlete of the Year award. However, the injuries that kept him out of club play also seriously damaged his aspirations for the national team.