| 28 Feb 23 | r02        | Portland TimbersPortland Timb | 1 - 0 | Sporting Kansas CitySporting Kans |
| 04 Mar 23 | r02        | Los Angeles FCLos Angeles F | 3 - 2 | Portland TimbersPortland Timb |
| |
| 12 Mar 23 | r04        | Portland TimbersPortland Timb | 1 - 2 | St. Louis City SCSt. Louis Cit |
| |
| 18 Mar 23 | r05        | Atlanta UnitedAtlanta Unite | 5 - 1 | Portland TimbersPortland Timb |
| |
| 25 Mar 23 | r06        | Portland TimbersPortland Timb | 0 - 0 | L.A. GalaxyL.A. Galaxy |
| |
| 02 Apr 23 | r08        | FC DallasFC Dallas | 1 - 1 | Portland TimbersPortland Timb |
| |
| 09 Apr 23 | r10        | Vancouver WhitecapsVancouver Whi | 1 - 0 | Portland TimbersPortland Timb |
| |
| 16 Apr 23 | r11        | Portland TimbersPortland Timb | 4 - 1 | Seattle Sounders FCSeattle Sound |
| |
| 23 Apr 23 | r12        | FC CincinnatiFC Cincinnati | 2 - 1 | Portland TimbersPortland Timb |
| |
| 30 Apr 23 | r14        | St. Louis City SCSt. Louis Cit | 1 - 2 | Portland TimbersPortland Timb |
| |
| 07 May 23 | r16        | Portland TimbersPortland Timb | 2 - 2 | Austin FCAustin FC |
| |
| 14 May 23 | r17        | Portland TimbersPortland Timb | 3 - 1 | Vancouver WhitecapsVancouver Whi |
| |
| 18 May 23 | r18        | Real Salt LakeReal Salt Lak | 0 - 0 | Portland TimbersPortland Timb |
| |
| 21 May 23 | r20        | Portland TimbersPortland Timb | 0 - 1 | Minnesota UnitedMinnesota Uni |
| |
| 28 May 23 | r21        | Sporting Kansas CitySporting Kans | 4 - 1 | Portland TimbersPortland Timb |
| |
| 03 Jun 23 | r23        | Seattle Sounders FCSeattle Sound | 0 - 0 | Portland TimbersPortland Timb |
| |
| 12 Jun 23 | r25        | Portland TimbersPortland Timb | 1 - 0 | FC DallasFC Dallas |
| |
| 18 Jun 23 | r26        | San Jose EarthquakesSan Jose Eart | 0 - 0 | Portland TimbersPortland Timb |
| |
| 22 Jun 23 | r27        | Portland TimbersPortland Timb | 1 - 2 | Chicago FireChicago Fire |
| |
| 25 Jun 23 | r29        | Portland TimbersPortland Timb | 1 - 1 | New York City FCNew York City |
| |
| 02 Jul 23 | r30        | Minnesota UnitedMinnesota Uni | 4 - 1 | Portland TimbersPortland Timb |
| |
| 13 Jul 23 | r31        | Colorado RapidsColorado Rapi | 0 - 0 | Portland TimbersPortland Timb |
| |
| 16 Jul 23 | r34        | Portland TimbersPortland Timb | 3 - 2 | Columbus CrewColumbus Crew |
| |
| 21 Aug 23 | r35        | Houston DynamoHouston Dynam | 5 - 0 | Portland TimbersPortland Timb |
| |
| 27 Aug 23 | r37        | Portland TimbersPortland Timb | 2 - 3 | Vancouver WhitecapsVancouver Whi |
| |
| 31 Aug 23 | r38        | Portland TimbersPortland Timb | 2 - 1 | Real Salt LakeReal Salt Lak |
| |
| 03 Sep 23 | r40        | Seattle Sounders FCSeattle Sound | 2 - 2 | Portland TimbersPortland Timb |
| 10 Sep 23 | r40        | Portland TimbersPortland Timb | 2 - 0 | Los Angeles FCLos Angeles F |
| |
| 18 Sep 23 | r42        | Austin FCAustin FC | 1 - 2 | Portland TimbersPortland Timb |
| |
| 21 Sep 23 | r43        | Portland TimbersPortland Timb | 2 - 1 | San Jose EarthquakesSan Jose Eart |
| |
| 24 Sep 23 | r44        | Portland TimbersPortland Timb | 3 - 2 | Colorado RapidsColorado Rapi |
| |
| 01 Oct 23 | r46        | L.A. GalaxyL.A. Galaxy | 3 - 3 | Portland TimbersPortland Timb |
| |
| 08 Oct 23 | r47        | CF MontréalCF Montréal | 4 - 1 | Portland TimbersPortland Timb |
| |
| 22 Oct 23 | r49        | Portland TimbersPortland Timb | 1 - 3 | Houston DynamoHouston Dynam |