| 18 Apr 21 | r01        | DC UnitedDC United | 2 - 1 | New York CityNew York City |
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| 24 Apr 21 | r02        | New York CityNew York City | 5 - 0 | FC CincinnatiFC Cincinnati |
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| 02 May 21 | r04        | Philadelphia UnionPhiladelphia | 0 - 2 | New York CityNew York City |
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| 09 May 21 | r05        | Orlando CityOrlando City | 1 - 1 | New York CityNew York City |
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| 15 May 21 | r06        | New York CityNew York City | 1 - 1 | Toronto FCToronto FC |
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| 23 May 21 | r08        | New York CityNew York City | 1 - 2 | Columbus CrewColumbus Crew |
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| 29 May 21 | r10        | Los Angeles FCLos Angeles F | 1 - 2 | New York CityNew York City |
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| 19 Jun 21 | r11        | New York CityNew York City | 2 - 3 | New England Rev.New England R |
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| 23 Jun 21 | r12        | New York CityNew York City | 1 - 0 | Atlanta UnitedAtlanta Unite |
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| 27 Jun 21 | r14        | New York CityNew York City | 2 - 1 | DC UnitedDC United |
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| 08 Jul 21 | r16        | CF MontréalCF Montréal | 2 - 1 | New York CityNew York City |
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| 18 Jul 21 | r17        | Columbus CrewColumbus Crew | 2 - 1 | New York CityNew York City |
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| 21 Jul 21 | r18        | New York CityNew York City | 1 - 0 | CF MontréalCF Montréal |
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| 25 Jul 21 | r20        | New York CityNew York City | 5 - 0 | Orlando CityOrlando City |
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| 31 Jul 21 | r21        | New York CityNew York City | 4 - 1 | Columbus CrewColumbus Crew |
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| 05 Aug 21 | r23        | Chicago FireChicago Fire | 0 - 0 | New York CityNew York City |
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| 08 Aug 21 | r24        | Toronto FCToronto FC | 2 - 2 | New York CityNew York City |
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| 15 Aug 21 | r25        | New York CityNew York City | 2 - 0 | Inter MiamiInter Miami |
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| 19 Aug 21 | r26        | Philadelphia UnionPhiladelphia | 1 - 0 | New York CityNew York City |
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| 29 Aug 21 | r29        | New York CityNew York City | 2 - 0 | New England Rev.New England R |
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| 04 Sep 21 | r30        | Nashville SCNashville SC | 3 - 1 | New York CityNew York City |
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| 12 Sep 21 | r31        | New England Rev.New England R | 2 - 1 | New York CityNew York City |
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| 14 Sep 21 | r32        | New York CityNew York City | 3 - 3 | FC DallasFC Dallas |
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| 19 Sep 21 | r33        | FC CincinnatiFC Cincinnati | 1 - 2 | New York CityNew York City |
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| 23 Sep 21 | r28        | New York Red BullsNew York Red | 1 - 1 | New York CityNew York City |
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| 26 Sep 21 | r35        | New York CityNew York City | 0 - 1 | New York Red BullsNew York Red |
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| 30 Sep 21 | r36        | Chicago FireChicago Fire | 2 - 0 | New York CityNew York City |
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| 03 Oct 21 | r38        | New York CityNew York City | 0 - 0 | Nashville SCNashville SC |
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| 17 Oct 21 | r40        | New York Red BullsNew York Red | 1 - 0 | New York CityNew York City |
| 21 Oct 21 | r40        | Atlanta UnitedAtlanta Unite | 1 - 1 | New York CityNew York City |
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| 24 Oct 21 | r41        | New York CityNew York City | 6 - 0 | DC UnitedDC United |
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| 28 Oct 21 | r43        | New York CityNew York City | 1 - 0 | Chicago FireChicago Fire |
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| 30 Oct 21 | r44        | Inter MiamiInter Miami | 1 - 3 | New York CityNew York City |
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| 07 Nov 21 | r46        | New York CityNew York City | 1 - 1 | Philadelphia UnionPhiladelphia |
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| 21 Nov 21 | Playoff        | New York CityNew York City | 2 - 0 | Atlanta UnitedAtlanta Unite |
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| 01 Dec 21 | QF        | New England Rev.New England R | 2 - 2 | New York CityNew York City |
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| 05 Dec 21 | SF        | Philadelphia UnionPhiladelphia | 1 - 2 | New York CityNew York City |
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| 11 Dec 21 | Final        | Portland TimbersPortland Timb | 1 - 1 | New York CityNew York City |