Portland Pilots (): kila uhamisho wa kuingia na kutoka, ada zilizolipwa na kupatikana, na thamani ya soko ya kikosi.
| Tarehe | Mchezaji | Kutoka | Kwenda | Ada |
|---|---|---|---|---|
| 2024-12-20 | Nick Fernández | Portland Pilots | SJ Earthquakes | Huru |
| 2024-05-01 | Nick Fernández | Portland Pilots | River Light FC | Mkopo |
| 2023-08-01 | Jerome Tibbling Ugwo | Portland Pilots | PAEEK Kyrenia | Huru |
| 2023-05-01 | Nick Fernández | Portland Pilots | Chicago City SC | Mkopo |
| 2022-08-01 | Jerome Tibbling Ugwo | Seton Hall | Portland Pilots | Huru |
| 2022-05-01 | Nick Fernández | Portland Pilots | Chicago City SC | Mkopo |
| 2020-08-01 | Nick Fernández | Barca Academy | Portland Pilots | Huru |
| 2019-01-01 | Benji Michel | Portland Pilots | Orlando | Huru |
| 2018-05-01 | Benji Michel | Portland Pilots | P. Timbers U23 | Mkopo |
| 2016-07-01 | Benji Michel | Orlando Academy | Portland Pilots | Huru |