2009 was a landmark season for the Barons in the Open Cup as they qualified for the Open Cup for the fourth time in the last six years. But the biggest highlight was the fact that Ocean City faced off with a club from Major League Soccer for the first time in franchise history. The Barons’ run in the tournament began with a shocking 3–0 home upset of Crystal Palace Baltimore of the USL Second Division. Byron Carmichael was named TheCup.us Player of the Round after scoring a pair of first half goals and J. T. Noone would put the nail in the coffin with a second half goal. The upsets at The Beach House continued in Round 2 when the Barons’ Tunde Ogunbiyi shutout the Real Maryland Monarchs of the Second Division and Noone converted a penalty kick in the second period of overtime to put the Barons into the third round by a score of 1–0. With the win, Ocean City became only the sixth amateur team in Open Cup history to register back-to-back wins over professional teams. In Round 3, the Barons would put a scare into D.C. United but would fall 2–0 to the defending Open Cup champs on a wet night at the Maryland SoccerPlex in Germantown, Maryland.