[2] The San Jose Earthquakes again won the tournament on their return to the MLS in 2008 while Real Salt Lake claimed the title in their debut in 2009.

The cup was not held in 2016, instead opting to hold individual friendly matches with Saint Louis FC, Wilmington Hammerheads and the New York Cosmos.

A highlight of the competitions that have been held so far is the Coffee Pot Cup, a game between D.C. United and the host Charleston Battery, making it a rare example of an MLS-USL team rivalry.

The history behind this comes from a postgame incident after the Third Round of the 1999 U.S. Open Cup, where Charleston pulled a shocking 4-3 extra time upset at home over D.C. A news report from then: "D.C. United apparently used the visitors' locker room to vent its frustration over losing to the Charleston Battery in last Wednesday's US Open Cup match at Blackbaud Stadium here.

Most recently the teams competed in the final of the 2008 Lamar Hunt U.S. Open Cup, as D.C. United defeated Charleston 2–1 on September 3, 2008, at RFK Stadium.