[8] Portland Timbers II 5-6 Ventura County FC [4] 2024-06-10 00:00
Stadium: Hillsboro Stadium Round: 1
Head to Head
| USA MLS Next Pro League | 2023/08/10 02:30 | Portland Timbers II v Ventura County FC | W | 6-1 |
| USA MLS Next Pro League | 2023/05/22 00:00 | Ventura County FC v Portland Timbers II | L | 2-0 |
| USA USL Championship | 2020/08/27 00:00 | Portland Timbers II v Ventura County FC | L | 2-3 |
| USA USL Championship | 2019/07/29 01:00 | Portland Timbers II v Ventura County FC | L | 1-2 |
| USA USL Championship | 2019/03/31 02:00 | Ventura County FC v Portland Timbers II | L | 3-2 |
| USA USL Championship | 2018/07/28 20:00 | Ventura County FC v Portland Timbers II | W | 3-4 |
| USA USL Championship | 2018/05/18 18:00 | Portland Timbers II v Ventura County FC | W | 7-3 |
| USA USL Championship | 2017/10/08 02:30 | Ventura County FC v Portland Timbers II | L | 3-2 |
| USA USL Championship | 2017/07/09 21:00 | Portland Timbers II v Ventura County FC | L | 3-4 |
| USA USL Championship | 2016/08/07 02:30 | Ventura County FC v Portland Timbers II | W | 3-4 |
| USA USL Championship | 2016/07/16 21:00 | Portland Timbers II v Ventura County FC | L | 1-4 |