[18] Portland Timbers II 1-3 San Jose Earthquakes II [10] 2024-03-23 02:30
Stadium: Hillsboro Stadium Round: 1
Head to Head
| USA MLS Next Pro League | 2023/05/28 21:00 | The Town v Portland Timbers II | W | 1-2 |
| USA MLS Next Pro League | 2023/04/03 00:00 | Portland Timbers II v The Town | L | 0-2 |
| USA MLS Next Pro League | 2022/07/22 20:00 | Portland Timbers II v The Town | L | 1-2 |
| USA MLS Next Pro League | 2022/05/08 21:00 | The Town v Portland Timbers II | L | 3-0 |
| USA MLS Next Pro League | 2022/03/31 02:00 | Portland Timbers II v The Town | L | 0-2 |
Home History
| USA US Open Cup | 2024/03/20 02:30 | Portland Timbers II v El Farolito | L | 1-2 |
| USA MLS Next Pro League | 2024/03/16 01:00 | Real Monarchs SLC v Portland Timbers II | D | 0-0 |
| USA MLS Next Pro League | 2023/09/24 21:00 | Portland Timbers II v Real Monarchs SLC | W | 2-1 |
| USA MLS Next Pro League | 2023/09/16 02:00 | Los Angeles FC II v Portland Timbers II | L | 4-0 |
| USA MLS Next Pro League | 2023/09/11 02:00 | Portland Timbers II v Houston Dynamo II | L | 1-3 |
| USA MLS Next Pro League | 2023/09/05 03:00 | Tacoma Defiance v Portland Timbers II | L | 4-0 |
| USA MLS Next Pro League | 2023/08/28 02:00 | Portland Timbers II v Colorado Rapids II | W | 2-0 |
| USA MLS Next Pro League | 2023/08/19 00:00 | St Louis City II v Portland Timbers II | L | 4-1 |
Away History
| USA MLS Next Pro League | 2024/03/18 00:00 | Ventura County FC v The Town | L | 2-1 |
| USA MLS Next Pro League | 2023/10/09 01:30 | Colorado Rapids II v The Town | L | 1-0 |
| USA MLS Next Pro League | 2023/10/01 22:00 | St Louis City II v The Town | W | 0-2 |
| USA MLS Next Pro League | 2023/09/24 21:00 | The Town v Los Angeles FC II | W | 1-0 |
| USA MLS Next Pro League | 2023/09/16 21:00 | Vancouver Whitecaps II v The Town | W | 2-5 |
| USA MLS Next Pro League | 2023/09/11 02:00 | Tacoma Defiance v The Town | L | 3-2 |
| USA MLS Next Pro League | 2023/09/04 02:00 | The Town v Minnesota United FC II | D | 2-2 |
| USA MLS Next Pro League | 2023/08/27 23:00 | St Louis City II v The Town | L | 3-1 |