Portland Pilots: every transfer in and out, fees paid and earned, squad market value.
| Date | Player | From | To | Fee |
|---|---|---|---|---|
| 2024-12-20 | Nick Fernández | Portland Pilots | SJ Earthquakes | Free |
| 2024-05-01 | Nick Fernández | Portland Pilots | River Light FC | Loan |
| 2023-08-01 | Jerome Tibbling Ugwo | Portland Pilots | PAEEK Kyrenia | Free |
| 2023-05-01 | Nick Fernández | Portland Pilots | Chicago City SC | Loan |
| 2022-08-01 | Jerome Tibbling Ugwo | Seton Hall | Portland Pilots | Free |
| 2022-05-01 | Nick Fernández | Portland Pilots | Chicago City SC | Loan |
| 2020-08-01 | Nick Fernández | Barca Academy | Portland Pilots | Free |
| 2019-01-01 | Benji Michel | Portland Pilots | Orlando | Free |
| 2018-05-01 | Benji Michel | Portland Pilots | P. Timbers U23 | Loan |
| 2016-07-01 | Benji Michel | Orlando Academy | Portland Pilots | Free |