Some players are difference-makers. They change games, no matter who they play for, helping turn slim losses to draws and disappointing draws to wins.
Juan Carlos Obregon Jr., captain of USL League One side Westchester SC, is one of these players.
“The mindset is different,” he said of playing in the Open Cup, a single-elimination tournament where a winner is required every time out. “It’s always win or go home. Winner takes it all, so you end up in situations where anything can happen and you have to put in your best performance at all times.”
Open Cup games require a healthy dose of winning attitude. Belief. Whether you’re playing against a team from a division below you, above you – or from the same level. And Obregon has been making all the difference for his first-year Div. III pro side in the first two Rounds of this year’s Open Cup.
He scored the only goal in Westchester’s First Round game, out on the road against historic amateur spoilers FC Motown in New Jersey on March 18. It was the first game in the history of the club, part-owned by USMNT star and 2017 Open Cup Runner-up Tyler Adams, and Obregon’s cool spot-kick ten minutes from time kept it from turning into a debut to forget.
In the Second Round, he wasted no time making his mark early – scoring the opening goal in a 3-2 win over another complicated amateur outfit in three-time Open Cup-Champion NY Pancyprian Freedoms.
Big Influence in Westchester & Beyond
The versatile forward, who’s happy to drop into the creative hole between midfield and frontline, has his fingerprints all over the team’s passage to the Third Round of the 2025 U.S. Open Cup. The New Yorkers now face a road trip to USL Championship (Div. II) side Detroit City FC and one of the toughest road tests in American soccer at the cauldron of Keyworth Stadium in Hamtramck.
