U.S. Open Cup Round of 16 Fixtures Set for May 20-21

The Lamar Hunt U.S. Open Cup, the oldest ongoing soccer competition in the United States, has reached its Round of 16. Scheduled for May 20 and 21, the upcoming stage features 15 clubs from Major League Soccer and one determined underdog from the USL Championship, Pittsburgh Riverhounds SC, the only lower-division team still standing.

Now in its 110th edition, the U.S. Open Cup has crowned national champions since 1914, offering a single-elimination format that blends professional ambition with grassroots passion. The winning club not only lifts the historic Dewar Challenge Trophy, but also earns a berth in the 2026 CONCACAF Champions Cup, securing its place among the continent’s elite.

This year’s bracket includes regional showdowns and budding rivalries. Austin FC and Houston Dynamo will clash in a Texas derby, while Philadelphia Union face Pittsburgh Riverhounds SC in a Keystone State duel that adds a layer of underdog drama. In the Midwest, Minnesota United host St. Louis CITY SC in a contest between two emerging forces, and in Washington, D.C. United take on Charlotte FC.

With defending champions LAFC already eliminated, the field is wide open. A record $1 million prize pool, including $600,000 for the eventual champion, further raises the stakes in a tournament that continues to blend tradition, opportunity, and unpredictability.

Key Round of 16 Matches (ET):

Tuesday, May 20:

• New England Revolution vs. Chicago Fire – 7:30 p.m.
• San Jose Earthquakes vs. Portland Timbers – 10:30 p.m.

Wednesday, May 21:

• New York Red Bulls vs. FC Dallas – 7:30 p.m.
• Philadelphia Union vs. Pittsburgh Riverhounds – 7:30 p.m.
• Austin FC vs. Houston Dynamo – 9:00 p.m.