Quest for MLS Cup begins tonight vs Chicago

The 2025 Supporters’ Shield winners open their MLS Cup Playoff account at home this Sunday against the Chicago Fire. The Philadelphia Union, who finished the regular season with a franchise-record 20 wins, look to continue their historic run by taking care of the red-hot Fire, who enter the postseason for the first time since 2017.

The best-of-three series against Chicago marks a matchup of two first-year managers with their respective sides. Gregg Berhalter, after navigating the twists and turns of his stint with the United States Men’s National Team, finished the regular season with 53 points, including nine crucial road wins to claim the eighth seed in the Eastern Conference. Meanwhile, Bradley Carnell capped off his inaugural season with the Boys in Blue with 66 points, boasting the best defense in the league with only 35 goals conceded and setting a club record with eight road victories.

Chicago punched its ticket to Chester last Wednesday by defeating Orlando City SC 3–1. The match began with a goal from homegrown talent Brian Gutiérrez early in the second half. From there, the Fire took complete control. A brace from Hugo Cuypers tripled the lead before Orlando’s consolation goal, capping off a perfect night in the Windy City for Berhalter’s side.

Much of Chicago’s success has been built on the shoulders of attackers Hugo Cuypers, who finished the MLS season with 19 goals, and Philip Zinckernagel, who added 15 of his own. Fortuitously for the Union, Fire goalkeeper Chris Brady has averaged 1.8 goals conceded per game with only five clean sheets this season, providing a prime opportunity for Philadelphia’s attack to capitalize.

The Union, although coming off a 2–0 loss to Charlotte, aim to get ahead early on Sunday. Tai Baribo, who stumbled slightly after his early lead in the Golden Boot race, still sits on 16 goals this season. Additionally, the midseason addition of Milan Iloski provides extra firepower for the Union, who are in desperate need after homegrown star Quinn Sullivan tore his ACL in one of the final away matches of the season against D.C. United. The key for Philadelphia will be catching the Fire early and relying on their league-best defense to see out the series.

The match kicks off a best-of-three series against the Fire, with the next match set to take place in the Windy City. A spot in the Eastern Conference Semifinal will be on the line for Sunday’s victor.

You can catch the match for free on MLS Season Pass with an Apple TV subscription at 5:30 p.m.