Timbers Academy (): every transfer in and out, fees paid and earned, and the market value of the squad.
| Date | Player | From | To | Fee |
|---|---|---|---|---|
| 2024-01-09 | Sawyer Jura | Timbers Academy | Portland 2 | — |
| 2021-01-01 | Hunter Sulte | Timbers Academy | Portland | — |
| 2020-03-06 | Hunter Sulte | Timbers Academy | Portland 2 | Loan |
| 2019-03-08 | Hunter Sulte | Timbers Academy | Portland 2 | Loan |
| 2016-01-01 | Marco Farfán | Timbers Academy | Portland 2 | — |