| 2023-07-02 | Minnesota UnitedvPortland TimbersMLS · United States | 4–1 | MLS · United States |
| 2023-06-25 | Portland TimbersvNew York CityMLS · United States | 1–1 | MLS · United States |
| 2023-06-22 | Portland TimbersvChicago FireMLS · United States | 1–2 | MLS · United States |
| 2023-06-18 | San Jose EarthquakesvPortland TimbersMLS · United States | 0–0 | MLS · United States |
| 2023-06-12 | Portland TimbersvFC DallasMLS · United States | 1–0 | MLS · United States |
| 2023-06-03 | Seattle SoundersvPortland TimbersMLS · United States | 0–0 | MLS · United States |
| 2023-05-28 | Sporting Kansas CityvPortland TimbersMLS · United States | 4–1 | MLS · United States |
| 2023-05-21 | Portland TimbersvMinnesota UnitedMLS · United States | 0–1 | MLS · United States |
| 2023-05-18 | Real Salt LakevPortland TimbersMLS · United States | 0–0 | MLS · United States |
| 2023-05-14 | Portland TimbersvVancouver WhitecapsMLS · United States | 3–1 | MLS · United States |
| 2023-05-07 | Portland TimbersvAustin FCMLS · United States | 2–2 | MLS · United States |
| 2023-04-30 | St. Louis CityvPortland TimbersMLS · United States | 1–2 | MLS · United States |
| 2023-04-23 | FC CincinnativPortland TimbersMLS · United States | 2–1 | MLS · United States |
| 2023-04-16 | Portland TimbersvSeattle SoundersMLS · United States | 4–1 | MLS · United States |
| 2023-04-09 | Vancouver WhitecapsvPortland TimbersMLS · United States | 1–0 | MLS · United States |
| 2023-04-02 | FC DallasvPortland TimbersMLS · United States | 1–1 | MLS · United States |
| 2023-03-25 | Portland TimbersvLos Angeles GalaxyMLS · United States | 0–0 | MLS · United States |
| 2023-03-18 | Atlanta UtdvPortland TimbersMLS · United States | 5–1 | MLS · United States |
| 2023-03-12 | Portland TimbersvSt. Louis CityMLS · United States | 1–2 | MLS · United States |
| 2023-03-04 | Los Angeles FCvPortland TimbersMLS · United States | 3–2 | MLS · United States |
| 2023-02-28 | Portland TimbersvSporting Kansas CityMLS · United States | 1–0 | MLS · United States |
| 2022-10-09 | Real Salt LakevPortland TimbersMLS · United States | 3–1 | MLS · United States |
| 2022-10-02 | Portland TimbersvLos Angeles FCMLS · United States | 1–2 | MLS · United States |
| 2022-09-18 | Columbus CrewvPortland TimbersMLS · United States | 1–1 | MLS · United States |
| 2022-09-11 | Portland TimbersvMinnesota UnitedMLS · United States | 1–0 | MLS · United States |
| 2022-09-04 | Portland TimbersvAtlanta UtdMLS · United States | 2–1 | MLS · United States |
| 2022-09-01 | Austin FCvPortland TimbersMLS · United States | 1–2 | MLS · United States |
| 2022-08-27 | Portland TimbersvSeattle SoundersMLS · United States | 2–1 | MLS · United States |
| 2022-08-22 | Sporting Kansas CityvPortland TimbersMLS · United States | 4–1 | MLS · United States |
| 2022-08-14 | Toronto FCvPortland TimbersMLS · United States | 3–1 | MLS · United States |
| 2022-08-07 | Portland TimbersvFC DallasMLS · United States | 1–1 | MLS · United States |
| 2022-08-04 | Portland TimbersvNashville SCMLS · United States | 1–1 | MLS · United States |
| 2022-07-30 | Minnesota UnitedvPortland TimbersMLS · United States | 4–4 | MLS · United States |
| 2022-07-24 | Portland TimbersvSan Jose EarthquakesMLS · United States | 2–1 | MLS · United States |
| 2022-07-18 | Portland TimbersvVancouver WhitecapsMLS · United States | 1–1 | MLS · United States |
| 2022-07-09 | Seattle SoundersvPortland TimbersMLS · United States | 0–3 | MLS · United States |
| 2022-07-04 | Nashville SCvPortland TimbersMLS · United States | 2–2 | MLS · United States |
| 2022-06-30 | Portland TimbersvHouston DynamoMLS · United States | 2–1 | MLS · United States |
| 2022-06-26 | Portland TimbersvColorado RapidsMLS · United States | 3–0 | MLS · United States |
| 2022-06-18 | Los Angeles GalaxyvPortland TimbersMLS · United States | 1–1 | MLS · United States |
| 2022-05-29 | Inter MiamivPortland TimbersMLS · United States | 2–1 | MLS · United States |
| 2022-05-23 | Portland TimbersvPhiladelphia UnionMLS · United States | 0–2 | MLS · United States |
| 2022-05-19 | San Jose EarthquakesvPortland TimbersMLS · United States | 3–2 | MLS · United States |
| 2022-05-15 | Portland TimbersvSporting Kansas CityMLS · United States | 7–2 | MLS · United States |
| 2022-05-08 | New York Red BullsvPortland TimbersMLS · United States | 1–1 | MLS · United States |
| 2022-05-01 | Colorado RapidsvPortland TimbersMLS · United States | 2–0 | MLS · United States |
| 2022-04-24 | Portland TimbersvReal Salt LakeMLS · United States | 0–0 | MLS · United States |
| 2022-04-16 | Houston DynamovPortland TimbersMLS · United States | 0–0 | MLS · United States |
| 2022-04-10 | Vancouver WhitecapsvPortland TimbersMLS · United States | 2–3 | MLS · United States |
| 2022-04-03 | Portland TimbersvLos Angeles GalaxyMLS · United States | 1–3 | MLS · United States |