November

• 21NovSabMLS Cup First Round: New England Revolution vs. Philadelphia Union - Home Game 1, Series Game 1Gillette Stadium14.00 (ET) · Foxborough
• 28NovSabMLS Cup First Round: Philadelphia Union vs. New England Revolution - Home Game 1, Series Game 2Subaru Park16.30 (ET) · Chester

Desember

• 2DesRabMLS Cup First Round: New England Revolution vs. Philadelphia Union - Home Game 2, Series Game 3 (Date: TBD - If Necessary)Gillette StadiumWaktu menyusul · Foxborough
• 5DesSabMLS Cup Conference Semifinal: Philadelphia Union vs. TBD (Date: TBD - If Necessary)Subaru ParkWaktu menyusul · Chester
• 11DesJumMLS Cup Conference Final: Philadelphia Union vs. TBD (Date: TBD - If Necessary)Subaru ParkWaktu menyusul · Chester

Februari 2027

• 20FebSabPhiladelphia Union vs. Chicago Fire FCSubaru Park13.00 (ET) · Chester
• 27FebSabColumbus Crew vs. Philadelphia UnionScottsMiracle-Gro Field13.00 (ET) · Columbus

Maret 2027

• 6MarSabNew York City FC vs. Philadelphia UnionYankee Stadium15.00 (ET) · Bronx
• 13MarSabPhiladelphia Union vs. New England RevolutionSubaru Park17.00 (ET) · Chester
• 17MarRabPhiladelphia Union vs. CF MontrealSubaru Park19.00 (ET) · Chester
• 27MarSabPhiladelphia Union vs. Charlotte FCSubaru Park19.00 (ET) · Chester

April 2027

• 3AprSabPhiladelphia Union vs. FC CincinnatiSubaru Park17.00 (ET) · Chester
• 7AprRabOrlando City SC vs. Philadelphia UnionInter&Co Stadium19.00 (ET) · Orlando
• 10AprSabD.C. United vs. Philadelphia UnionAudi Field19.00 (ET) · Washington
• 21AprRabPhiladelphia Union vs. New York Red BullsSubaru Park19.00 (ET) · Chester
• 24AprSabInter Miami CF vs. Philadelphia UnionNu Stadium at Miami Freedom Park19.00 (ET) · Miami

Mei 2027

• 1MeiSabPhiladelphia Union vs. Nashville SCSubaru Park19.00 (ET) · Chester
• 8MeiSabAtlanta United FC vs. Philadelphia UnionMercedes-Benz Stadium17.00 (ET) · Atlanta