2025 U.S. Open Cup Round of 16 schedule, best matchups | OneFootball

The U.S. Open Cup has reached the Round of 16, with MLS teams dominating the field following their introduction to the competition in the Fourth Round.

All but one of the 16 MLS teams competing advanced past their lower-division opponent earlier this week, the exception being the USL Championship's Pittsburgh Riverhounds home win over New York City FC.

The potential matchups and hosting priorities for the Round of 16 were already known heading into the Fourth Round, but now we have the full schedule.

Here are some of the most intriguing games coming up:

New England Revolution vs. Chicago Fire

The New England Revolution will be playing their second cup tie in Rhode Island in as many rounds, this time as the home side as they adopt Providence College as their adopted home turf. The 1,500-capacity Chapey Field at Anderson Stadium should be packed to the brim to welcome a Chicago Fire club that is in a three-way tie for most USOC titles won with four.

Philadelphia Union vs. Pittsburgh Riverhounds

The Riverhounds carry the lower division torch into an intriguing intrastate clash against the Union, who needed penalties to defeat Indy Eleven, one of Pittsburgh's USL colleagues. This will be the first-ever meeting between the sides. Philly's previous intrastate clashes have come against the now-defunct Harrisburg City Islanders.

Austin FC vs. Houston Dynamo

This will be the second meeting in four weeks between the Texan rivals after Houston earned a 2-0 victory at home in their first regular season clash. And there could be increased pressure on Austin manager Nico Estevez to earn a result if the Verde's recent dip in league form continues, during a stretch that includes games against FC Cincinnati and the Vancouver Whitecaps.

U.S. Open Cup Round of 16 schedule

All times Eastern (TV/Streaming in parentheses)

Tuesday, May 20

7:30 pm - New England Revolution vs. Chicago Fire (Paramount+, CBS Sports Golazo Network)10:30 pm - San Jose Earthquakes vs. Portland Timbers (Paramount+, CBS Sports Network)

Wednesday, May 21