Interview Series: Jimmy Filerman - A Career as Told in US Open Cup Matches

Eight years ago, a 19 year old Jimmy Filerman had his first experience in the US Open Cup as a player for the South Florida Surf in USL League Two. A team of mostly amateur players in their schools’ offseasons came together to face Miami FC, who at the time was spending big money to put together a competitive roster in the NASL with Manager Alessandro Nesta (of Italian National Team Fame).

The team of kids tied the game in the 76’ before Miami put the go-ahead goal away in the 80’. It was the type of game that makes this tournament so special. It gives young players the opportunity to test themselves against seasoned professionals. It puts David up against Goliath in a winner-take-all one match battle. It gives players that have given their youth to the game an experience they won’t forget. Lastly, it is truly the only open thing that exists in our world of soccer with a closed pyramid.

Jimmy would return back to Old Dominion for two more seasons after that and end his college career in 2019. Despite Covid doing its best to kill off parts of the fragile US Soccer Lower Leagues, he found a home in Detroit City in 2020 and 2021. He was part of those DCFC teams that completely dominated NISA. With Covid putting a pause on the Open Cup due to travel restrictions, there were no opportunities for him to play the tournament while playing for the club. But 2021 would take Filerman down to Greenville Triumph for his first experience playing in the professional ranks of USL.

It was here that he’d see US Open Cup action for the second time. Greenville triumphed (dad joke) over Oakland Roots for a first round cupset and that set up a home game for them against MLS’ Charlotte FC. The 4,000 person capacity stadium witnessed their 3rd Division squad take Charlotte to extra time where they eventually succumbed 2-1.

“They subbed in guys like Christian Fuchs” says Jimmy on the pod. “Just being on the field with guys you grew up watching, and those big entities where you know how much money they’re bringing in and how much money has gone into the roster is just different.”

After a broken leg ended his time at Greenville, Jimmy joined up with the Maryland Bobcats in 2023 and was part of a roster that took down the Ocean City Nor’easters on a last second winner before succumbing on the road to the Pittsburgh Riverhounds on a cold, wet night along the Monongahela River.

Fast forward to Jimmy in 2025 and a lot has changed. The 19 year old kid that admittedly loved him some College is now a 28 year old man that has had a lasting career in the 3rd and 4th divisions of the US Soccer Pyramid.

A lot has happened in those eight years. Things have come full circle for Jimmy as he returned to the Open Cup as an amateur 8 years after being there with South Florida Surf.

Jimmy linked back up with his DC United Academy running mate, Lucas Mendes, who is the creative force and visionary behind Virginia Dream FC. For those that do not know, the Dream have been quickly building up accommodates as one of the best Amateur sides in the country. The club won the NPSL Mid-Atlantic last year, the Spring and Fall 2024 UPSL Seasons, and the 2024 Virginia Super Soccer League. Then they qualified for the 2025 US Open Cup by beating Alexandria Reds and the Aegean Hawks FC of the United States Amateur Soccer Association (USASA).

The Dream came into City Stadium with a chip on their shoulders. A squad full of players that had been there before and players that know they should still be there (special shout out to Elijah Amo who absolutely needs a call from a pro side…). After an 8’ minute penalty kick was calmly slotted into the corner by former Bobcat Nicolas Likulia, it was clear Richmond was in for a fight from the pesky amateur side.

After a banger from the Kickers’ James Vaughn drew them equal in the 36’, the Dream held on to head into the locker room at 1-1. After taking some abuse in front of their goal at the end of the first half, the Dream became the aggressors and put home two more goals. One from Suchecki in the 53’ and another from former Bobcat Mike Akinkoye in the 61’. With the lead in hand and the armband on, Jimmy came alive and showed he still has what it takes to compete on this level. Making tackles and shouting instructions. The cupset was on.

When the final whistle blew, it was the Dream marching on to the next round of the 2025 US Open Cup. On Wednesday, April 2nd, the Dream head to Segra Field to take on its next Goliath; the USL Championships’ Loudoun United. While it will be another uphill battle, I wouldn’t count them out.