| 25 Feb 24 | r01        | Portland TimbersPortland Timb | 4 - 1 | Colorado RapidsColorado Rapi |
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| 03 Mar 24 | r03        | Portland TimbersPortland Timb | 2 - 2 | DC UnitedDC United |
| 09 Mar 24 | r03        | New York City FCNew York City | 1 - 2 | Portland TimbersPortland Timb |
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| 17 Mar 24 | r06        | Houston DynamoHouston Dynam | 1 - 0 | Portland TimbersPortland Timb |
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| 24 Mar 24 | r07        | Portland TimbersPortland Timb | 1 - 3 | Philadelphia UnionPhiladelphia |
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| 31 Mar 24 | r08        | Vancouver WhitecapsVancouver Whi | 3 - 2 | Portland TimbersPortland Timb |
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| 07 Apr 24 | r10        | Sporting Kansas CitySporting Kans | 3 - 3 | Portland TimbersPortland Timb |
| 13 Apr 24 | r10        | Portland TimbersPortland Timb | 2 - 2 | Los Angeles FCLos Angeles F |
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| 20 Apr 24 | r12        | Columbus CrewColumbus Crew | 2 - 2 | Portland TimbersPortland Timb |
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| 28 Apr 24 | r14        | Los Angeles FCLos Angeles F | 3 - 2 | Portland TimbersPortland Timb |
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| 04 May 24 | r15        | Charlotte FCCharlotte FC | 2 - 0 | Portland TimbersPortland Timb |
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| 12 May 24 | r17        | Portland TimbersPortland Timb | 1 - 2 | Seattle Sounders FCSeattle Sound |
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| 16 May 24 | r19        | Portland TimbersPortland Timb | 4 - 2 | San Jose EarthquakesSan Jose Eart |
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| 19 May 24 | r20        | Minnesota UnitedMinnesota Uni | 2 - 1 | Portland TimbersPortland Timb |
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| 26 May 24 | r21        | Portland TimbersPortland Timb | 2 - 1 | Sporting Kansas CitySporting Kans |
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| 30 May 24 | r22        | Austin FCAustin FC | 0 - 2 | Portland TimbersPortland Timb |
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| 02 Jun 24 | r24        | Portland TimbersPortland Timb | 2 - 2 | Houston DynamoHouston Dynam |
| 09 Jun 24 | r24        | St. Louis City SCSt. Louis Cit | 0 - 0 | Portland TimbersPortland Timb |
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| 20 Jun 24 | r27        | San Jose EarthquakesSan Jose Eart | 1 - 2 | Portland TimbersPortland Timb |
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| 23 Jun 24 | r28        | Portland TimbersPortland Timb | 2 - 0 | Vancouver WhitecapsVancouver Whi |
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| 30 Jun 24 | r30        | Portland TimbersPortland Timb | 3 - 2 | Minnesota UnitedMinnesota Uni |
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| 05 Jul 24 | r31        | FC DallasFC Dallas | 3 - 2 | Portland TimbersPortland Timb |
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| 08 Jul 24 | r33        | Portland TimbersPortland Timb | 4 - 1 | Nashville SCNashville SC |
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| 14 Jul 24 | r34        | Portland TimbersPortland Timb | 3 - 0 | Real Salt LakeReal Salt Lak |
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| 21 Jul 24 | r37        | L.A. GalaxyL.A. Galaxy | 3 - 2 | Portland TimbersPortland Timb |
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| 25 Aug 24 | r38        | Portland TimbersPortland Timb | 4 - 4 | St. Louis City SCSt. Louis Cit |
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| 01 Sep 24 | r39        | Portland TimbersPortland Timb | 1 - 0 | Seattle Sounders FCSeattle Sound |
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| 15 Sep 24 | r41        | Colorado RapidsColorado Rapi | 2 - 1 | Portland TimbersPortland Timb |
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| 19 Sep 24 | r43        | Portland TimbersPortland Timb | 4 - 2 | L.A. GalaxyL.A. Galaxy |
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| 22 Sep 24 | r44        | Real Salt LakeReal Salt Lak | 3 - 3 | Portland TimbersPortland Timb |
| 29 Sep 24 | r44        | Vancouver WhitecapsVancouver Whi | 1 - 1 | Portland TimbersPortland Timb |
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| 03 Oct 24 | r47        | Portland TimbersPortland Timb | 0 - 1 | Austin FCAustin FC |
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| 06 Oct 24 | r48        | Portland TimbersPortland Timb | 0 - 0 | FC DallasFC Dallas |
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| 20 Oct 24 | r50        | Seattle Sounders FCSeattle Sound | 1 - 1 | Portland TimbersPortland Timb |
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| 24 Oct 24 | r00        | Vancouver WhitecapsVancouver Whi | 5 - 0 | Portland TimbersPortland Timb |