Match Preview: Westchester SC vs Portland Hearts of Pine
- Randy Medina
- 6 days ago
- 5 min read
Updated: 5 days ago
Westchester SC Enters the Prinx Cup Fray
Prinx Cup Preview
We begin with an introduction to the USL Prinx Tires Cup. Just as our run in the US Open Cup comes to a close, here comes the league cup to fill the void. If readers aren’t familiar, think of it like this. If the US Open Cup is like the FA Cup in England, where basically anyone with 11 players and a ball can enter at the lower levels, the Prinx Cup functions more like the Carabao Cup. The field is tighter, the competition is more focused, and the margin for error shrinks quickly.
The 2026 Prinx Tires USL Cup is the third edition of the USL’s interleague competition, featuring all 43 teams across the USL Championship and League One in a World Cup style format. Teams are split into regional groups, playing four group stage matches before the knockout rounds begin later this summer.
Westchester SC has been drawn into Group 5 alongside:
New Jersey Cosmos
Seven group winners plus one wild card advance. That wild card goes to the best second-place team, with goals scored as the first tiebreaker. Translation: every game matters, and style points might actually count.
If you didn’t notice, most of our competition sits in the higher USL Championship. That means as a USL League One side, Westchester will spend a lot of time punching up. That makes matchups like this one against Portland, and upcoming games against the New Jersey Cosmos, all the more important. These are the games where you don’t just participate. You prove something.
Saturday’s Game
While it does not count toward the USL League One standings, Saturday marks our first real look at how we stack up against Portland this season.
Both clubs joined the league in 2025, but the paths have been very different. Portland benefitted from a two year runway and a region starving for professional sports, allowing them to build a strong fan base and identity early. That translated into a much stronger debut season than what Westchester experienced.
Now in year two, Westchester is hoping new signings and a more settled squad can begin to close that gap as the two sides meet for the first time in 2026.
Recent Form
Will the real Westchester SC please stand up?
The early season has been all over the place. Just when it looked like league form was starting to stabilize, the club stumbled badly, putting up what can only be described as a rotten potato on the scoreboard in Boise with a 0-4 loss to Athletic.
Getting Max Jennings back from suspension will help. The question is whether that alone is enough to steady things.
Portland Snapshot
Portland enters this one coming off a 1-1 draw against FC Naples in front of over 6,000 supporters at Fitzpatrick Stadium. Even in poor weather, the atmosphere remained loud and engaged, something that continues to define the club.
They started brightly, pressing high and creating chances early. A disallowed goal prevented them from grabbing immediate control, but they eventually broke through in the 36th minute through Ollie Wright. It was a notable moment, marking Portland’s first goal in over 400 minutes of play.
However, the match shifted in the second half. Portland lost control, dropped deeper, and eventually conceded a late equalizer in the 87th minute. Still, there were positives. Improved chemistry, sharper attacking movement, and a defensive structure that held up for long stretches.
In short, they are trending upward. Not dominant, but dangerous.
Players to Watch
Westchester SC
Back from suspension, Jennings immediately becomes the tone-setter for this side again. His return isn’t just about talent, it’s about structure. Westchester has looked far more settled when he’s on the pitch, particularly in how they transition from defense into attack. Expect him to be heavily involved early, looking to impose himself and reestablish rhythm after the Boise setback. If Westchester is going to control any part of this game, it likely runs through him.
Evans feels like one of those players who can tilt a match without needing a ton of touches. Direct, willing to run at defenders, and capable of creating something out of nothing, he gives Westchester an edge they’ve lacked at times this season. Against a Portland side that showed vulnerability when sitting deeper late against Naples, Evans could be the one to exploit tired legs and stretched lines.
Burko brings a bit of bite and balance to the attack. In a game where Westchester may spend stretches without the ball against a more established side, his ability to disrupt play and keep things ticking simply becomes critical. He doesn’t need to dominate the stat sheet to influence the match. If he’s doing his job, Portland will feel it.
BIG GAME ALERT
You already know the storyline.
Drack returns to face Westchester after a short and somewhat unfinished chapter with the club. He made an immediate impact for Portland in his last outing, showing attacking intent from the back and even playing a role in their goal before exiting with injury. If he’s fit, expect him to be flying up that flank with something to prove. These are the games players circle, and all signs point to him being right in the middle of it.
Randy’s Prediction
2-2 draw in the rain.
Feels chaotic, feels emotional, feels like both teams leave thinking they could have had more.
AI Prediction
Alright, let’s let the robots have a go at it.
Based on early season volatility from Westchester, Portland’s slightly more stable structure, and typical home field influence at Memorial Field, the numbers lean just slightly toward the visitors.
AI Prediction: Portland Hearts of Pine 2 – 1 Westchester SC
The model expects Portland to control longer stretches of possession and capitalize on one of those late-game moments where Westchester has struggled to stay compact. That said, it also flags this as a high-variance match, meaning an early goal from Westchester could flip everything on its head.
In other words, the AI doesn’t trust either of these teams fully yet. And honestly, neither do we.
Pre-Game Tailgate
Time & Location
April 25, 20263:00 PM to 6:00 PM
555 E Sandford Blvd, Mount Vernon, NY
Join us on Saturday as we get ready for Westchester SC taking on Portland Hearts of Pine.
We’ll be set up in the stadium parking lot, upper level, with everything you need to kick off matchday the right way.
Expect a proper supporters atmosphere with food, drinks, and plenty of energy as we build toward kickoff. Whether you’ve been with us from the start or you’re just finding your way in, this is the perfect place to connect, meet fellow supporters, and be part of the growing culture around the club.
Admission
Free for 914th Infantry members
$10 donation for non-members (Includes food & drink)
Game Info
Date:Â Saturday, April 25, 2026
Location:Â Memorial Field, Mount Vernon
Kickoff:Â 7:00 PM
Tickets:Â SeatGeek
Local TV:Â MSG Plus
Streaming:Â ESPN Plus
If the Open Cup run introduced people to what this club can be, this is where we find out what it actually is.