U.S. Open Cup Delivers Insane Drama in the Round of 16 | OneFootball

This was the first R16 that failed to feature multiple lower league teams, but what it lacked in #cupset potential, it more than made up for it with thrilling fixtures.

New England Revolution 1 – 3 Chicago Fire FC

The first half was pure forgettable trash, outside of a 38th minute Eric Klein own goal that put the hosts on the back foot. The second half wasn’t that much better, both sides seemingly content to trade possession in the midfield with the occasional offensive foray. When what appeared to be a Revs second own goal instead caromed off the post, Hugo Cuypers’ resulting volley showed spectacular skill, even if it was created by an element of luck. With a two goal lead, Fire settled into a groove. New England managed to pull back a goal in stoppage time.

San Jose Earthquakes 1 – 0 Portland Timbers

Who the hell is Jack Skahan? Even die-hard Earthquakes fans would be hard pressed to pick him out of a line-up. This unheralded midfielder has been with San Jose since 2021, but only started 18 games and scored a total of six goals. In 2024 he averaged 33 minutes per game; this season he logged 163 minutes prior to stepping on the pitch to replace Ousseni Bouda. But in the 116th minute he became a hero when he placed the slightest of touches onto Mark-Anthony Kaye’s shot to redirect it into the net. The result was only fair, as San Jose owned the stats line in shots (29 to 14), shots-on-goal (9 to 5) and corners (12 to 2).

D.C. United 3 (2) – 3 (1) Charlotte FC

There was miserable rain. Charlotte’s recent form has been miserable. D.C.’s season has been kinda miserable. So much misery concentrated in Audi Field, but this game was pure fire!

Not only were there four goals in regular time, there were goals from either side in the extra time! United’s Daniel Schnegg started it off with a perfect volley in the 17th. He was celebrating even before the net rippled. The Charlotte’s Patrick Agyemang took matters into his own feet, driving into the DC box and coolly slotting it home. Bill Tuiloma got his first goal for Charlotte off a corner in the 61st. Then DC United equalized in the 86th from Garrison Tubbs. Charlotte’s Tyger Smalls (brilliant name, BTW) put them up in extra time, but Jackson Hopkins pulled DC level shortly thereafter. In an interesting move, United actually subbed on goalkeeper Jordan Farr in the 120th minute.

With so much drama, the penalty shootout was bound to be exciting and it did not disappoint. D.C. drained their first two PKs, but then Charlotte keeper David Bingham saved the next three. But United’s substitution strategy proved to be a masterful bit of coaching. Jordan Farr stopped FOUR of the five Charlotte stops. FOUR. Any shootout with more than two stops is rare. Seven is insane.

This marks the third straight year Charlotte have been eliminated in the Open Cup Round of 16.

New York Red Bulls 2 (4) – 2 (3) FC Dallas

Fact: The Red Bulls came into this match having not lost to FC Dallas in 9 straight fixtures. But boy did it look like they would. Twice the Red Bulls had to come back. Mohammed Sofo got the first equalizer in the 62nd minute; Dallas responded with a Luciano Acosta goal 15 minutes later. With that, Dallas looked to be firmly in the driver’s seat, but Emil Forsberg’s free kick in the 93rd deflected off Cameron Harper and in the goal. Extra time saw Dallas go down to ten after Ramiro’s red card in the 113th, but they held on for the penalty shootout. Each keeper recorded one save from the spot, and it was Acosta’s opening panenka that rattled off the crossbar that gave New York the win.

Philadelphia Union 4 – 1 Pittsburgh Riverhounds

An early PK put the ‘Hounds in the kennel. Then Indiana Vassilev doubled the lead right before halftime. Pittsburgh might be the USL club with the best historical record against MLS clubs (4 wins and 7 losses), but the quality gap between these teams was glaringly obvious. Haitian midfielder Danly Jean Jacques got Union’s third. Pittsburgh’s Jorge Garcia hit a stunner in the 63rd from the corner of the goal box to give the visitors a brief hope. Brief was the operative word, as a defensive giveaway allowed Jovan Lukic to snatch the ball, then dribble into the box and score. Too easy. Pittsburgh gets $50K for advancing the farthest of any USL Championship club.

Orlando City SC 2 – 3 Nashville SC

Marco Pašalić hit an absolute banger for the purple, and his team had the run of play for most of the first half. But some slack defending conceded a own goal in the 23rd and then allowed Nashville to snatch a second from Ahmed Qasem’s strike. Orlando’s Romero Enrique put the sides level in the 58th, and once again they appeared to be in control. However, Nashville unleashed an utter golazo ten minutes from regulation, with Wyatt Meyers lacing it into the near corner off a stunning back-heeled pass from Patrick Yazbek. Despite a furious Orlando onslaught in the many minutes of stoppage, Nashville clung to the lead and brought the home side’s twelve game unbeaten streak to an end.

Minnesota United FC 3 – 2 St. Louis CITY SC

All season the Loons have not lost a game when scoring first. But CITY made a mockery of that in the second half. First it was Marcel Hartel heading in a cross in the 55th when Minnesota’s back line was ball-watching. Ten minutes later, Hartel’s deep cross found an unmarked João Klauss on the back post; his subsequent header slammed the ball downward and into the net.

But CITY failed to account for defender Anthony Markanich, twin brother of Nick (who scored 30 goals in the 2024 USL). In the 85th he drilled a screamer from a perfect through ball from Joaquín Pereyra. Minutes later the Loons had a chance when Tani Oluwaseyi got around the keeper but his ensuing shot was blocked off the line by Joshua Yero. In the subsequent corner, Markanich got a big leap and scored another to give Minnesota the lead. They held on, and in doing so issued St. Louis their eleventh straight winless match.

Austin FC 3 – 1 Houston Dynamo FC

Two red cards in the five minutes of stoppage ensured a dramatic finish to this hotly contested Texas derby. Austin took a three goal lead by the 60th minutes and appeared to be in cruise control. The Houston found some steel and pressured the hosts in the final 25 minutes after Ezequiel Ponce’s goal. Austin will advance into the quarterfinals for the first time in the club’s history.

Quarterfinals

The draw for the quarterfinals will be tomorrow, May 22nd at 9:30am ET. The games will be played in July.