

Team 2021 Scheduals| 18 Apr |
r02 | Columbus CrewColumbus Crew | 0 - 0 | Philadelphia UnionPhiladelphia |
| 25 Apr |
r03 | Philadelphia UnionPhiladelphia | 1 - 2 | Inter MiamiInter Miami |
| 01 May |
r04 | Philadelphia UnionPhiladelphia | 0 - 2 | New York CityNew York City |
| 08 May |
r05 | Chicago FireChicago Fire | 0 - 2 | Philadelphia UnionPhiladelphia |
| 13 May |
r06 ![]() | Philadelphia UnionPhiladelphia | 1 - 1 | New England Rev.New England R |
| 16 May |
r07 | Philadelphia UnionPhiladelphia | 1 - 0 | New York Red BullsNew York Red |
| 24 May |
r09 | DC UnitedDC United | 0 - 1 | Philadelphia UnionPhiladelphia |
| 30 May |
r10 | Philadelphia UnionPhiladelphia | 3 - 0 | Portland TimbersPortland Timb |
| 20 Jun |
r12 | Atlanta UnitedAtlanta Unite | 2 - 2 | Philadelphia UnionPhiladelphia |
| 23 Jun |
r12 | Philadelphia UnionPhiladelphia | 1 - 0 | Columbus CrewColumbus Crew |
| 27 Jun |
r13 | Chicago FireChicago Fire | 3 - 3 | Philadelphia UnionPhiladelphia |
| 04 Jul |
r15 | Nashville SCNashville SC | 1 - 0 | Philadelphia UnionPhiladelphia |
| 09 Jul |
r16 | New York Red BullsNew York Red | 1 - 1 | Philadelphia UnionPhiladelphia |
| 17 Jul |
r17 ![]() | Philadelphia UnionPhiladelphia | 2 - 1 | DC UnitedDC United |
| 22 Jul |
r19 | Orlando CityOrlando City | 2 - 1 | Philadelphia UnionPhiladelphia |
| 25 Jul |
r19 ![]() | Inter MiamiInter Miami | 1 - 1 | Philadelphia UnionPhiladelphia |
| 01 Aug |
r22 ![]() | Philadelphia UnionPhiladelphia | 1 - 1 | Chicago FireChicago Fire |
| 04 Aug |
r22 | Philadelphia UnionPhiladelphia | 3 - 0 | Toronto FCToronto FC |
| 08 Aug |
r24 | New England Rev.New England R | 2 - 1 | Philadelphia UnionPhiladelphia |
| 18 Aug |
r26 | Philadelphia UnionPhiladelphia | 1 - 0 | New York CityNew York City |
| 22 Aug |
r27 | Philadelphia UnionPhiladelphia | 1 - 1 | CF MontréalCF Montréal |
| 29 Aug |
r29 | DC UnitedDC United | 3 - 1 | Philadelphia UnionPhiladelphia |
| 03 Sep |
r32 | Philadelphia UnionPhiladelphia | 0 - 1 | New England Rev.New England R |
| 19 Sep |
r34 | Philadelphia UnionPhiladelphia | 3 - 1 | Orlando CityOrlando City |
| 25 Sep |
r35 | Philadelphia UnionPhiladelphia | 1 - 0 | Atlanta UnitedAtlanta Unite |
| 29 Sep |
r36 | New York Red BullsNew York Red | 1 - 1 | Philadelphia UnionPhiladelphia |
| 03 Oct |
r38 | Philadelphia UnionPhiladelphia | 3 - 0 | Columbus CrewColumbus Crew |
| 10 Oct |
r25 | FC CincinnatiFC Cincinnati | 1 - 2 | Philadelphia UnionPhiladelphia |
| 16 Oct |
r38 | CF MontréalCF Montréal | 2 - 2 | Philadelphia UnionPhiladelphia |
| 21 Oct |
r40 | Minnesota UnitedMinnesota Uni | 3 - 2 | Philadelphia UnionPhiladelphia |
| 23 Oct |
r42 | Philadelphia UnionPhiladelphia | 1 - 0 | Nashville SCNashville SC |
| 27 Oct |
r43 ![]() | Toronto FCToronto FC | 2 - 2 | Philadelphia UnionPhiladelphia |
| 31 Oct |
r44 | Philadelphia UnionPhiladelphia | 2 - 0 | FC CincinnatiFC Cincinnati |
| 07 Nov |
r46 | New York CityNew York City | 1 - 1 | Philadelphia UnionPhiladelphia |
| 20 Nov |
Playoff | Philadelphia UnionPhiladelphia | 1 - 0 | New York Red BullsNew York Red |
| 28 Nov |
QF | Philadelphia UnionPhiladelphia | 1 - 1 | Nashville SCNashville SC |
| 05 Dec |
SF | Philadelphia UnionPhiladelphia | 1 - 2 | New York CityNew York City |