MLS clubs were first included in the U.S. Open Cup tournament in 1996. D.C. United won the tournament that year, and repeated their success in 2008. In 2009, the club began its title defense in the MLS qualification rounds. This meant that they had to win six games instead of the four needed to obtain the cup in 2008.
In their first qualifying match on March 28, 2009, they hosted FC Dallas at RFK Stadium in Washington, D.C. They defeated Dallas 2–0, with Fred and Brandon Barklage scoring in the 21st and 66th minutes, respectively. D.C. United's second qualification match was also played at RFK Stadium, on May 20, 2009. In a high-scoring match against the New York Red Bulls, D.C. won 5–3. Chris Pontius scored two of United's five goals, qualifying D.C. for the third round of the official tournament.
On June 30, 2009, D.C. United began official cup competition against the Ocean City Barons of the USL Premier Development League. The match, hosted by United at Maryland SoccerPlex in Boyds, Maryland, ended with D.C. on top 2–0. As a fourth-tier club, the Barons lineup had featured amateur players while United's included only three regular starters. The match remained scoreless for 74 minutes before D.C. took the lead on a penalty kick by late substitution Christian Gomez. One week later, on July 7, D.C. United hosted their quarterfinal match at the SoccerPlex again and defeated the Harrisburg City Islanders of the USL Second Division 2–1. On July 21, 2009, D.C. United hosted another lower tier team in their semifinal match at the SoccerPlex. This time they defeated the Rochester Rhinos of the USL First Division 2–1. The match was tied 1–1 until the 82nd minute when Boyzzz Khumalo's goal propelled D.C. into the cup final.
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