The Barons bounced back from a disappointing 2008 season with one of the club’s greatest campaigns in 2009. In addition to a pair of professional team upsets in the U.S. Open Cup and a date with D.C. United of Major League Soccer, Ocean City had a great regular season and a historic postseason run. After a 9–4–3 record earned them a third-place finish in the competitive Northeast Division and a spot in the postseason, they made history with two playoff wins before advancing to the PDL quarterfinals. The Barons eliminated the Long Island Rough Riders, the second best defensive team in the PDL, 2–0 in the opening round, giving OC their first playoff win since 2004. In the next round, the Men In Red handed the undefeated Ottawa Fury their first loss of the season with a 2–1 overtime win on a 98th-minute goal by Tyler Bellamy. The playoff run came to an end in Des Moines, Iowa, where they lost to the Chicago Fire Premier 3–0.