Eskandarian played his first four MLS seasons for D.C. United, who drafted him #1 overall in the 2003 MLS Superdraft. During his first season he recorded three goals and two assists in 23 games. In the 2004 season, after the replacement of coach Ray Hudson with Peter Nowak, Eskandarian saw significantly more playing time. In his sophomore campaign, Eskandarian led D.C. United in goal scoring with ten in the regular season and added two assists, while scoring 4 more goals in the playoffs as DC United won the 2004 MLS Cup. His strong play also earned him the D.C. United Coaches Award for 2004 and his first spot on the MLS All-Star team.