Portland Hearts of Pine stepped away from their League One schedule and into Prinx Tires USL Cup play, making the trip to West Vernon, New York to take on fellow USL1 side Westchester SC in a match played through a steady deluge. Coming off a 1–1 draw with Naples FC, the Hearts carried momentum into a night that ultimately ended in a 2–2 draw, with Westchester claiming the extra point in a 5–4 penalty shootout. 

Portland entered the match shorthanded in the goalkeeping department, with backup Kash Oladapo unavailable due to a red card issued in the 2025 USL Cup against Pittsburgh Riverhounds SC. The club signed Brunswick, Maine native Peter Morrell to serve as Hunter Morse’s backup. Portland was also without newly signed Josh Drack.  

Portland wasted little time asserting themselves. Hearts pressed the pace early, immediately testing Westchester keeper Andrew Hammersley. Emiliano Terzaghi forced a save that was pushed out for a corner, and from that sequence, Portland struck. Matteo Kidd sent a low, driven ball across the face of goal that found Esteban Espinosa, who buried a header from close range in the 7th minute to give Portland a 1–0 lead. 

For much of the opening stretch, Portland controlled the tempo, but the match turned in the 23rd minute. 

Westchester’s Kyle Evans broke free down the touchline and, after initially being slowed by Brecc Evans slipped past him and drew Mo Mohamed into a questionable challenge inside the box. The contact resulted in a penalty. Conor McGlynn converted the kick, sending Morse the wrong way to level the match at 1–1. 

Portland nearly leveled the match in the 32nd minute; Kidd’s free kick deflected out to Ollie Wright, who struck a clean effort from 18 yards, only to see Hammersley dive and gather it at the near post. Moments later, Hearts dodged disaster.

After Kidd tracked back to disrupt another Kyle Evans run, a casual pass back toward Morse nearly resulted in a goal, but the keeper recovered just in time, getting a foot on Evans’ attempt and sending the ball high into the rain before it was cleared. 

The second half brought a shift in momentum. 

Portland looked to inject more attacking energy, bringing on JayTee Kamara but it was Westchester that struck next. In the 50th minute, a ball played up the flank found Kyle Evans, who slipped it across to an unmarked Daniel Burko near the goal area. Burko finished, chipping it over Morse, despite Portland’s appeals for offside, to give Westchester a 2–1 lead. 

As it seemed the match might slip away, Ollie Wright delivered. In the 84th minute, Wright sent a ball in from distance that appeared to catch Hammersley flat-footed. What appeared to be a service toward Titus Washington instead slid into the far side of the net, leveling the match at 2–2. It marked Wright’s third goal in three matches. 

With no winner after 90 minutes, the match went straight to penalties to determine who would earn the extra point in Group 6. The shootout was tense and back-and-forth. Wright, perfect from the spot entering the match, converted Portland’s opener, matched by Westchester’s Dean Guezen. Portland stumbled in the second round as Brecc Evans was denied by Hammersley, allowing Westchester to take the edge when Daniel Burko converted. 

Both sides traded successful penalties through the middle rounds, JayTee Kamara and Koen Blommestijn converting, followed by Konstantinos Georgallides and a key save from Morse on Jonathan Jiménez to keep Portland alive. Kemali Green and Daniel Bouman each found the net, setting up a dramatic finish. 

With the shootout extending, Brecc Evans was once again turned away by Hammersley, opening the door for Westchester. Aleksei Armas stepped up and delivered, firing past a diving Morse to secure the 5–4 shootout victory. 

In the end, Portland leaves with a point from the draw but will feel it let an opportunity slip. A strong start, a late equalizer, and moments of control were not quite enough to overcome the penalty setback. The result places the Hearts in a tie for fourth after the opening round of USL Cup group play, with plenty still to be decided, but little margin for error moving forward. 

Portland will face USL Championship side Rhode Island FC at Fitzpatrick Stadium May 16, in the next round of the Prinx Tires USL Cup.