Portland Pilots (): cada chegada e saída, valores pagos e recebidos, e o valor de mercado do plantel.
| Data | Jogador | De | Para | Verba |
|---|---|---|---|---|
| 2024-12-20 | Nick Fernández | Portland Pilots | SJ Earthquakes | Livre |
| 2024-05-01 | Nick Fernández | Portland Pilots | River Light FC | Empréstimo |
| 2023-08-01 | Jerome Tibbling Ugwo | Portland Pilots | PAEEK Kyrenia | Livre |
| 2023-05-01 | Nick Fernández | Portland Pilots | Chicago City SC | Empréstimo |
| 2022-08-01 | Jerome Tibbling Ugwo | Seton Hall | Portland Pilots | Livre |
| 2022-05-01 | Nick Fernández | Portland Pilots | Chicago City SC | Empréstimo |
| 2020-08-01 | Nick Fernández | Barca Academy | Portland Pilots | Livre |
| 2019-01-01 | Benji Michel | Portland Pilots | Orlando | Livre |
| 2018-05-01 | Benji Michel | Portland Pilots | P. Timbers U23 | Empréstimo |
| 2016-07-01 | Benji Michel | Orlando Academy | Portland Pilots | Livre |