[13] LA Galaxy II 2-0 Portland Timbers II [12] 2023-05-22 00:00
Stadium: Dignity Health Sports Park Round: 1
Head to Head
| USA - USL Championship | 2020/08/27 00:00 | Portland Timbers II v Ventura County FC | W | 2-3 |
| USA - USL Championship | 2019/07/29 01:00 | Portland Timbers II v Ventura County FC | W | 1-2 |
| USA - USL Championship | 2019/03/31 02:00 | Ventura County FC v Portland Timbers II | W | 3-2 |
| USA - USL Championship | 2018/07/28 20:00 | Ventura County FC v Portland Timbers II | L | 3-4 |
| USA - USL Championship | 2018/05/18 18:00 | Portland Timbers II v Ventura County FC | L | 7-3 |
| USA - USL Championship | 2017/10/08 02:30 | Ventura County FC v Portland Timbers II | W | 3-2 |
| USA - USL Championship | 2017/07/09 21:00 | Portland Timbers II v Ventura County FC | W | 3-4 |
| USA - USL Championship | 2016/08/07 02:30 | Ventura County FC v Portland Timbers II | L | 3-4 |
Home History
| USA - MLS Next Pro League | 2023/05/14 22:00 | Sporting Kansas City II v Ventura County FC | L | 2-1 |
| USA - MLS Next Pro League | 2023/05/08 00:00 | Ventura County FC v Colorado Rapids II | L | 0-5 |
| USA - MLS Next Pro League | 2023/05/01 03:00 | Tacoma Defiance v Ventura County FC | L | 3-1 |
| USA - MLS Next Pro League | 2023/04/24 00:00 | Ventura County FC v Austin FC II | W | 6-5 |
| USA - MLS Next Pro League | 2023/04/17 00:00 | Vancouver Whitecaps II v Ventura County FC | W | 3-4 |
| USA - MLS Next Pro League | 2023/04/10 00:00 | Ventura County FC v Minnesota United FC II | L | 1-2 |
| USA - MLS Next Pro League | 2023/04/03 00:00 | Ventura County FC v North Texas SC | L | 0-1 |
| USA - MLS Next Pro League | 2023/03/27 00:00 | The Town v Ventura County FC | L | 3-0 |
Away History
| USA - MLS Next Pro League | 2023/05/14 23:00 | Portland Timbers II v Vancouver Whitecaps II | W | 3-1 |
| USA - MLS Next Pro League | 2023/05/08 00:00 | Portland Timbers II v Austin FC II | L | 0-1 |
| USA - MLS Next Pro League | 2023/04/30 22:00 | Real Monarchs SLC v Portland Timbers II | L | 5-1 |
| USA - MLS Next Pro League | 2023/04/24 00:00 | Portland Timbers II v Los Angeles FC II | W | 2-0 |
| USA - MLS Next Pro League | 2023/04/10 02:00 | Colorado Rapids II v Portland Timbers II | L | 4-2 |
| USA - MLS Next Pro League | 2023/04/03 00:00 | Portland Timbers II v The Town | L | 0-2 |
| USA - MLS Next Pro League | 2023/03/27 02:00 | Vancouver Whitecaps II v Portland Timbers II | L | 2-1 |
| USA - MLS Next Pro League | 2022/09/18 23:00 | Tacoma Defiance v Portland Timbers II | W | 0-2 |