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Philadelphia Union are playing with house money as MLS Cup playoffs resume

With expectations for 2025 already exceeded, the Philadelphia Union are playing with house money. Three home wins in a row would secure the club's first-ever MLS Cup!

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The Philadelphia Union are back in action this weekend after a three-week break, following the first round of the playoffs, which the MLS incorporates into its scheduling, as they host the Eastern Conference Semifinals against New York City FC.

As the top seed in the league, Philly will host every playoff game the rest of the way should they advance.  They're three wins away from hosting MLS Cup in front of the home fans at Subaru Park.  Who would've thought of that before the season started?

Tai Baribo celebrates as the Chicago fans watch on as the Philadelphia Union takes an early lead in the 8th minute of game two of round one of the 2025 MLS Cup playoffs.
Tai Baribo celebrates as the Chicago fans watch on as the Philadelphia Union takes an early lead in the 8th minute of game two of round one of the 2025 MLS Cup playoffs.
Image Provided / Philadelphia Union

Union playing with house money

Philly was not expected to be good this year. Many pundits expected this team to finish as a road playoff team or outside of the playoff field. Philly flipped that on its head with a first-year head coach who helped the team return to a gegenpressing style of soccer. The young and hungry roster bought in and executed throughout 34 games to become the best team in the league.

Now, they won their first round best-of-three series with Chicago in two games, and take on NYCFC with the chance to start a historic three-game run. We are so far past what many thought this team could be, from a mid-table team to a legitimate MLS Cup contender.

When we looked at expectations for this season before a ball was kicked, it was clear that the barometer for success was to be competitive, make the playoffs, use the homegrown players appropriately, and reset the team's vibes. On the field, this team has exceeded essentially all expectations.

Oct 26, 2025; Chester, Pennsylvania, USA; Philadelphia Union forward Milan Iloski (32) celebrates his goal with Philadelphia Union midfielder Indiana Vassilev (19) and Philadelphia Union forward Tai Baribo (9) in the second half against the Chicago Fire at Subaru Park. Mandatory Credit: James Lang-Imagn Images
Oct 26, 2025; Chester, Pennsylvania, USA; Philadelphia Union forward Milan Iloski (32) celebrates his goal with Philadelphia Union midfielder Indiana Vassilev (19) and Philadelphia Union forward Tai Baribo (9) in the second half against the Chicago Fire at Subaru Park. Mandatory Credit: James Lang-Imagn Images
James Lang

A look back at Preseason expectations

Back before the season started, we at Philly Sports Network set realistic expectations for this team. We looked at what a baseline success, an unmitigated failure, and an overarching success would be for five categories: MLS Play, US Open Cup, Player Development, Coaching Tactics, and Culture & Vibes. Here's a look back at it all.

  1. MLS Play
    Baseline Success: Make the playoffs.
    Unmitigated Failure: Miss playoffs for a 2nd season in a row.
    Overarching Success: Finish top four in the East.
  2. US Open Cup
    Baseline Success: Make the Quarterfinals.
    Unmitigated Failure: Get knocked out in the first match.
    Overarching Success: Play in the US Open Cup Final for the 4th time in Club history.
  3. Player Development
    Baseline Success: Play the Kids... appropriately.
    Unmitigated Failure: Play few Homegrowns OR Play Homegrowns who aren't ready for 1st team minutes.
    Overarching Success: Find the correct balance of minutes for Homegrowns to balance out veterans.
  4. Coaching Tactics
    Baseline Success: Sticking to the system and making game-dictated changes.
    Unmitigated Failure: Only having a Plan A and never-ever changing.
    Overarching Success: Executing an Energy-Drink pressing style to become an elite team
  5. Culture & Vibes
    Baseline Success: Field a competitive team that fans can connect with.
    Unmitigated Failure: Ostracize the fans when they voice their complaints.
    Overarching Success: Get the fans to buy into the team's system while winning matches.

Of these five categories, it looks like the Union has achieved overarching success in all but the US Open Cup, where they reached the semifinals, a baseline success. This team's success, hoisting a Supporters' Shield and getting past the first round of the playoffs, coupled with the fact that everyone counted them out since day one, shows that Philly isn't feeling the pressure that some number-one overall seeds have felt in previous MLS Cup Playoffs. The question is, can they win the whole damn thing?

The Philadelphia Union are the 2025 MLS Supporters' Shield winners after securing the best record in MLS
The Philadelphia Union are the 2025 MLS Supporters' Shield winners after securing the best record in MLS
Image Provided / Philadelphia Union

The pressure is off; can Philly's fight outlast the big spenders & star players?

The Union doesn't have a big-name star. They have moneyballed their way and implemented a system of play that has dominated MLS in 2025. Winning three home games and lifting the MLS Cup would make it the most successful season in club history. To do so, they'll need to beat teams with big-spending clubs that rely on the talents of star players.

Should Philly get past a strong rival, NYCFC will be about the team's collective grit. New York is similar to Philly, but it spends more money on their roster.  The reward for getting past them, which isn't a given at all, would pit Philadelphia against Cincinnati and Evander, or Miami and Messi-and-friends in the conference finals. Can Philly's press stop them and carry them to a home MLS Cup final? The chances to take on the likes of Vancouver, LAFC, San Diego, or Minnesota still pit an underdog Philly against higher spenders and superstars.

This all sounds daunting, but the union has shown, time and time again this year, that they are up to the task. There's no pressure, there's just 90 minutes on the field. The time for a cup run is now; let's see if Philly can defy even more odds and win the Cup.

Union, Philadelphia Union, MLS, MLS Cup Playoffs