| 2026-05-24 | Portland TimbersvSan Jose EarthquakesMLS · United States | 1–3 | MLS · United States |
| 2026-05-17 | Inter MiamivPortland TimbersMLS · United States | 2–0 | MLS · United States |
| 2026-05-14 | CF MontrealvPortland TimbersMLS · United States | 2–2 | MLS · United States |
| 2026-05-10 | Portland TimbersvSporting Kansas CityMLS · United States | 6–0 | MLS · United States |
| 2026-05-02 | Real Salt LakevPortland TimbersMLS · United States | 2–0 | MLS · United States |
| 2026-04-26 | San Diego FCvPortland TimbersMLS · United States | 1–2 | MLS · United States |
| 2026-04-19 | Minnesota UnitedvPortland TimbersMLS · United States | 2–0 | MLS · United States |
| 2026-04-11 | Portland TimbersvLos Angeles FCMLS · United States | 2–1 | MLS · United States |
| 2026-04-05 | Vancouver WhitecapsvPortland TimbersMLS · United States | 3–2 | MLS · United States |
| 2026-03-22 | Portland TimbersvLos Angeles GalaxyMLS · United States | 1–1 | MLS · United States |
| 2026-03-15 | Houston DynamovPortland TimbersMLS · United States | 3–2 | MLS · United States |
| 2026-03-08 | Portland TimbersvVancouver WhitecapsMLS · United States | 1–4 | MLS · United States |
| 2026-02-28 | Colorado RapidsvPortland TimbersMLS · United States | 2–0 | MLS · United States |
| 2026-02-22 | Portland TimbersvColumbus CrewMLS · United States | 3–2 | MLS · United States |