All countries
| Real Monarchs | Portland Timbers 2 | 4:1 (1:1, 3:0) | details | 13.06.2026 | ||||
| Vancouver Whitecaps 2 | Portland Timbers 2 | 0:1 (0:0, 0:1) | details | 06.06.2026 | ||||
| Portland Timbers 2 | Tacoma Defiance | 1:0 (1:0, 0:0) | details | 31.05.2026 | ||||
| Portland Timbers 2 | Houston Dynamo 2 | 0:3 (0:1, 0:2) | details | 24.05.2026 | ||||
| San Jose Earthquakes II | Portland Timbers 2 | 0:1 (0:0, 0:1) | details | 18.05.2026 | ||||
| Portland Timbers 2 | Minnesota 2 | 2:1 (0:0, 2:1) | details | 14.05.2026 | ||||
| Portland Timbers 2 | Ventura County | 3:4 AfP (1:2, 2:1, 6:7) | details | 10.05.2026 | ||||
| Real Monarchs | Portland Timbers 2 | 0:3 (0:1, 0:2) | details | 03.05.2026 | ||||
| Portland Timbers 2 | North Texas | 2:3 AfP (0:1, 2:1, 3:5) | details | 19.04.2026 | ||||
| Los Angeles FC 2 | Portland Timbers 2 | 0:1 (0:1, 0:0) | details | 16.04.2026 | ||||
| Portland Timbers 2 | Ventura County | 0:1 AfP (0:0, 0:0, 7:8) | details | 24.03.2026 | ||||
| Houston Dynamo 2 | Portland Timbers 2 | 5:0 (3:0, 2:0) | details | 16.03.2026 | ||||
| Portland Timbers 2 | Vancouver Whitecaps 2 | 1:0 AfP (0:0, 0:0, 7:6) | details | 08.03.2026 | ||||
| Portland Timbers 2 | San Jose Earthquakes II | 2:1 (0:1, 2:0) | details | 01.03.2026 | ||||
| Portland Timbers 2 | St. Louis City 2 | 2:1 (2:0, 0:1) | details | 05.10.2025 | ||||
| Austin FC II | Portland Timbers 2 | 1:2 (1:1, 0:1) | details | 27.09.2025 | ||||
| Houston Dynamo 2 | Portland Timbers 2 | 3:1 (1:0, 2:1) | details | 22.09.2025 | ||||
| Portland Timbers 2 | Los Angeles FC 2 | 5:3 (1:2, 4:1) | details | 14.09.2025 | ||||
| San Jose Earthquakes II | Portland Timbers 2 | 3:2 AfP (1:2, 1:0, 4:3) | details | 07.09.2025 | ||||
| Vancouver Whitecaps 2 | Portland Timbers 2 | 4:1 (3:0, 1:1) | details | 01.09.2025 | ||||
| Portland Timbers 2 | Tacoma Defiance | 2:1 (1:1, 1:0) | details | 25.08.2025 | ||||
| Colorado Rapids 2 | Portland Timbers 2 | 1:0 (0:0, 1:0) | details | 21.08.2025 | ||||
| Ventura County | Portland Timbers 2 | 3:2 AfP (2:0, 0:2, 6:5) | details | 10.08.2025 | ||||
| Portland Timbers 2 | Real Monarchs | 1:2 (1:0, 0:2) | details | 04.08.2025 | ||||
| Tacoma Defiance | Portland Timbers 2 | 1:2 (0:2, 1:0) | details | 28.07.2025 | ||||
| Portland Timbers 2 | Minnesota 2 | 2:1 AfP (1:1, 0:0, 5:3) | details | 19.07.2025 | ||||
| Los Angeles FC 2 | Portland Timbers 2 | 1:0 (0:0, 1:0) | details | 14.07.2025 | ||||
| Sporting Kansas City II | Portland Timbers 2 | 0:4 (0:0, 0:4) | details | 05.07.2025 | ||||
| Portland Timbers 2 | Austin FC II | 1:2 AfP (1:0, 0:1, 4:5) | details | 21.06.2025 | ||||
| Portland Timbers 2 | Ventura County | 2:3 (2:3, 0:0) | details | 12.06.2025 | ||||
| Real Monarchs | Portland Timbers 2 | 4:1 (2:0, 2:1) | details | 29.05.2025 | ||||
| St. Louis City 2 | Portland Timbers 2 | 6:3 (1:2, 5:1) | details | 24.05.2025 | ||||
| Portland Timbers 2 | Tacoma Defiance | 2:1 (2:1, 0:0) | details | 19.05.2025 | ||||
| Portland Timbers 2 | Los Angeles FC 2 | 3:0 (2:0, 1:0) | details | 15.05.2025 | ||||
| Portland Timbers 2 | Vancouver Whitecaps 2 | 1:0 (0:0, 1:0) | details | 09.05.2025 | ||||
| San Jose Earthquakes II | Portland Timbers 2 | 5:0 (3:0, 2:0) | details | 05.05.2025 | ||||
| Ventura County | Portland Timbers 2 | 2:3 (1:1, 1:2) | details | 24.04.2025 | ||||
| Portland Timbers 2 | Colorado Rapids 2 | 1:2 (1:0, 0:2) | details | 13.04.2025 | ||||
| Portland Timbers 2 | North Texas | 1:2 (1:1, 0:1) | details | 05.04.2025 | ||||
| Vancouver Whitecaps 2 | Portland Timbers 2 | 2:1 AfP (0:0, 1:1, 5:4) | details | 30.03.2025 | ||||
| Portland Timbers 2 | San Jose Earthquakes II | 2:1 AfP (0:0, 1:1, 4:3) | details | 27.03.2025 | ||||
| Portland Timbers 2 | Real Monarchs | 2:3 (1:2, 1:1) | details | 16.03.2025 | ||||
| Colorado Rapids 2 | Portland Timbers 2 | 0:1 (0:0, 0:1) | details | 06.10.2024 | ||||
| Real Monarchs | Portland Timbers 2 | 2:0 (0:0, 2:0) | details | 30.09.2024 | ||||
| Portland Timbers 2 | Ventura County | 2:1 (0:1, 2:0) | details | 18.09.2024 | ||||
| Portland Timbers 2 | Los Angeles FC 2 | 2:3 (2:0, 0:3) | details | 14.09.2024 | ||||
| Tacoma Defiance | Portland Timbers 2 | 5:2 (0:0, 5:2) | details | 09.09.2024 | ||||
| Portland Timbers 2 | San Jose Earthquakes II | 1:2 (1:1, 0:1) | details | 01.09.2024 | ||||
| Los Angeles FC 2 | Portland Timbers 2 | 3:2 AfP (1:1, 1:1, 5:3) | details | 17.08.2024 | ||||
| Portland Timbers 2 | Austin FC II | 4:3 AfP (3:2, 0:1, 8:7) | details | 09.08.2024 | ||||