It’s been a while since the Chicago Fire won a trophy (2006 to be exact), but they are four-time Champions of our Open Cup and on the hunt to become the first-ever five-time winner from the MLS Era. Led by former USMNT head coach Gregg Berhalter, they’ve had their wobbles to start the MLS season, and they won’t have things all their own way up against noted giant-killers Detroit City FC of the USL Championship.
WATCH Chicago Fire (Div. I) v Detroit City FC (Div. II) on Paramount+
Last but never least among our former Champs is Houston Dynamo – who lifted this country’s most historic prize in 2018, led by DaMarcus Beasley, and again in 2023 with Mexico legend Hector Herrera bossing the on-field action. The head coach now (same as in 2023) is Ben Olsen. “Trophies talk,” said Olsen, who faces what he called a “tough draw” on the road against Phoenix Rising FC of the USL Championship. “When the fans see you holding a trophy, it’s special. And that doesn’t go away,”
WATCH Phoenix Rising (Div. II) v Houston Dynamo (Div. I) on Paramount+
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Union Omaha’s Owls – Division III Kings of the Cupset
Any devoted fans of Open Cup Chaos, the Magic of the Cup – or whatever you want to call it – will have eyes glued on Union Omaha when they travel to take on MLS side St. Louis CITY SC at Energizer Park. The Division III Owls of Nebraska are among the most dangerous underdogs in recent Open Cup history – and their thin OT loss to eventual Finalists Sporting KC last year in the Round of 32 is evidence of what they can do out on the field – regardless of the opponent.
“We like the role of underdogs when we’re going up against a team from MLS,” said Dion Acoff, who scored the winning goal in the side’s Cupset win over Div. II San Antonio FC in the last round – and was also part of the Union Omaha team that beat two MLS sides in 2022 en route to the Quarterfinals. “We can just play freely, give it our best shot and hope things fall with us.”
The game will be a replay of the same fixture that saw 22, 423 fans turn out in St. Louis in 2023.
WATCH St. Louis CITY SC (Div. I) v Union Omaha (Div. III) on Paramount+
Elsewhere on Day Two (Wednesday, May 6) is a series of USL Championship vs. MLS matchups posing big jeopardy for the Division I sides. New York City FC travel to Highmark Stadium, on the banks of the Monongahela River, to meet noted Upset-Weavers the Pittsburgh Riverhounds. Hounds fans will remember that run to the Quarterfinals in 2023 that was sparked by wins over the New England Revolution (on the road) and Columbus Crew at home at Highmark.
WATCH Pitt. Riverhounds (Div. II) v NYCFC (Div. I) on Paramount+
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Also on the road, Minnesota United FC – our 2019 Open Cup Runners-up – will have their hands full against Louisville City FC at their Lynn family Stadium. The Kentucky side have a huge reputation in the Division II USL Championship – and, with the experienced Danny Cruz at the helm, they’re aiming at matching their best-ever Open Cup finish earned in 2022 (Round of 16).
Then there’s the Philadelphia Union. Our three-time losing Finalists have a home date against Indy Eleven, our top-performing Division II side from last year who stormed all the way to the Semifinals in a historic run for the Indiana club.
WATCH Louisville City (Div. II) v Minnesota United FC (Div. I) on Paramount+
WATCH Philadelphia Union (Div. I) v Indy Eleven (Div. II)
Out west, we finish with two more potential banana skins for MLS’ big boys. First up, Austin FC open their doors to El Paso Locomotive in an all-Texas showdown. The Austin side, who only played their first Open Cup game in 2019, haven’t had much in the way of success. Neither have the Locomotive – until this year, that is. The El Paso-based club, who never won an Open Cup game in years of trying, won three times so far in 2025 and are led by the steady hand of 2018 Open Cup-winning boss (with Houston Dynamo) Wilmer Cabrera.
“We’re improving and growing as a team,” said the former Colombia international and World Cup participant (1998) who overhauled the roster and got the El Paso side humming. “You try to do your best, because you want to go far in the U.S. Open Cup.”
We close out our Round of 32 action in San Jose, with another battle between MLS’ San Jose Earthquakes – coached now by former USMNT boss Bruce Arena, who won the Open Cup with D.C. United in the 1990s – hosting Sacramento Republic. The Div. II side knocked the Quakes out of two of the last three Open Cups and stormed through to a shock Final appearance in 2022.
“These types of games are what you play for,” said returning Sacramento legend Rodrigo ‘RoRo’ Lopez, who tore his ACL in last year’s Open Cup win over San Jose. “It’s also a rivalry and I think they are going to remember the last few years and how the results have gone. It’s now our turn to be the underdogs and go out there and perform.”
WATCH Phoenix Rising (Div. II) v Houston Dynamo (Div. I) on Paramount+
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WATCH on air at CBS Sports Network
WATCH San Jose Quakes (Div. I) v Sacramento Republic (Div. II) on Paramount+
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Fontela is editor-in-chief of ussoccer.com/us-open-cup. Follow him at@jonahfontela on X/Twitter.
