[13] San Jose Earthquakes II 1-2 Portland Timbers II [14] 2023-05-28 21:00
Stadium: PayPal Park Round: 1
Head to Head
| VS - MLS Next Pro League | 2023/04/03 00:00 | Portland Timbers II v The Town | W | 0-2 |
| VS - MLS Next Pro League | 2022/07/22 20:00 | Portland Timbers II v The Town | W | 1-2 |
| VS - MLS Next Pro League | 2022/05/08 21:00 | The Town v Portland Timbers II | W | 3-0 |
| VS - MLS Next Pro League | 2022/03/31 02:00 | Portland Timbers II v The Town | W | 0-2 |
Home History
| VS - MLS Next Pro League | 2023/05/26 02:00 | The Town v Vancouver Whitecaps II | L | 0-1 |
| VS - MLS Next Pro League | 2023/05/20 01:00 | Austin FC II v The Town | W | 0-1 |
| VS - MLS Next Pro League | 2023/05/13 02:00 | The Town v North Texas SC | W | 5-3 |
| VS - MLS Next Pro League | 2023/05/06 02:00 | The Town v Sporting Kansas City II | L | 1-2 |
| VS - MLS Next Pro League | 2023/04/30 22:30 | Los Angeles FC II v The Town | W | 0-1 |
| VS - MLS Next Pro League | 2023/04/17 00:00 | The Town v Colorado Rapids II | L | 0-2 |
| VS - MLS Next Pro League | 2023/04/10 00:00 | The Town v Real Monarchs SLC | L | 0-1 |
| VS - MLS Next Pro League | 2023/04/03 00:00 | Portland Timbers II v The Town | W | 0-2 |
Away History
| VS - MLS Next Pro League | 2023/05/26 02:00 | Portland Timbers II v St Louis City II | L | 1-2 |
| VS - MLS Next Pro League | 2023/05/22 00:00 | Ventura County FC v Portland Timbers II | L | 2-0 |
| VS - MLS Next Pro League | 2023/05/14 23:00 | Portland Timbers II v Vancouver Whitecaps II | W | 3-1 |
| VS - MLS Next Pro League | 2023/05/08 00:00 | Portland Timbers II v Austin FC II | L | 0-1 |
| VS - MLS Next Pro League | 2023/04/30 22:00 | Real Monarchs SLC v Portland Timbers II | L | 5-1 |
| VS - MLS Next Pro League | 2023/04/24 00:00 | Portland Timbers II v Los Angeles FC II | W | 2-0 |
| VS - MLS Next Pro League | 2023/04/10 02:00 | Colorado Rapids II v Portland Timbers II | L | 4-2 |
| VS - MLS Next Pro League | 2023/04/03 00:00 | Portland Timbers II v The Town | L | 0-2 |