Led by Ray Hudson, D.C. United's 2003 campaign was highlighted by the club's return to the MLS Cup Playoffs, their first postseason appearance since 1999. In the playoffs, United who didn't qualify for the playoffs until the final day of the regular season, took on the Eastern Conference regular season champions, Chicago Fire. The Fire defeated United 4–0 on aggregates in the conference semifinals, winning each leg by a 2–0 margin of victory.

On November 1, 2003, D.C. United played their first playoff match in nearly four years, entering the 2003 MLS Cup Playoffs as the fourth seed in the Eastern Conference. In the Conference semifinals, United faced the Eastern Conference regular season champions, Chicago Fire. The two-match, aggregate series was first contested at United's RFK Stadium. The match ended in a 2–0 defeat thanks to goals from the Fire's Andy Williams and Ante Razov in the 4th and 94th minutes, respectively.

A week later, on November 9, 2003, the second leg was played at Chicago Fire's Soldier Field, where the Fire defeated United by the same 2–0 scoreline, thus ultimately winning the series 4–0 on aggregate, and advancing to the Eastern Conference championship. The defeat ended United's playoff campaign and their season altogether.

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