On November 14, 2004, Eskandarian played in his first MLS Cup game. He helped D.C. United defeat the Kansas City Wizards and win the championship by scoring two goals in the first half just four minutes apart — the fastest pair of goals in MLS Cup history — and was named the MLS Cup MVP. In 2005, Alecko's season ended early after suffering a concussion. After missing most of 2005 with post-concussion syndrome, Eskandarian wasted no time in making his mark on the 2006 season, scoring against New York in the season opener. In 22 games for D.C. United, Eskandarian recorded seven goals and two assists, including Goal of the Week honors on 5/13 for his tally against KC. His impressive return to form netted Eskandarian a Commissioner's Pick as an MLS All-Star, his second nod to the league's showcase event. On August 9, 2006, during the 2006 Summer Tour of Real Madrid, he scored DC United's only goal in a 1-1 draw with Real Madrid.