The fans bested the staffers 3-1 in the 2013 River Cup, and raised money for the club's charitable arm.
Played at the Union's PPL Park, the game had all the trappings of a real match, with the video board, public address system, and a full officiating crew deployed for the occasion. There was even a supporter's section, albeit one which seemed to be rooting against both sides.
The Union front office - captained by majority owner Jay Sugarman and featuring team CEO Nick Sakiewicz and head coach John Hackworth - went up first as academy coach Kevin Coleman nodded home a rebounded corner kick. But the Sons of Ben came back to win 3-1, and nearly made it four when the front office goalkeeper, VP of Ticket Sales Mike Quarino, channeled former Union keeper Chris Seitz and let a soft ball get under him only to gratefully see it roll into the post.
More importantly, the event and the festivities surrounding it raised tens of thousands of dollars for the Philadelphia Union Foundation, the team's charitable arm.
"All of the proceeds go to programs we do in the city, which are centered around soccer for the kids, education for the kids, and facilities for the kids," said Sakiewicz. "Our foundation's giving is centered around those three things.
"For this match, I think we're going to push $40,000, which is almost double what we did last year.
Asked if the game brought back memories of his time as a professional goalkeeper, Sakiewicz, now 52, laughed. "It's nothing like my good old days. I've got 52 years on my legs and everything now seems a lot slower than it was when I played.
"I was actually a pretty good player in my good old days, and I don't pretend I'm a pretty good player anymore."
The Sons of Ben were delighted to hoist the trophy for the first time in the game's three-year history.
"(Expletive) right, dude," said captain Corey Furlan. "It's about time, absolutely fantastic. I'm on top of the world, everybody busted their bags out there, we did what we had to do.
"(The charitable nature of the mach) is the biggest thing though. It's about raising money for charity, absolutely."