| DLD. Letayf | In | 2026-08-16 | Free agent | — | PP Portland Hearts of Pine |
FR Felipe Rodriguez-Gentile | In | 2026-08-13 | Free agent | PR Preston PRE | PPPortland Hearts of Pine |
| FRFelipe Rodriguez-Gentile | In | 2026-08-12 | Free agent | PRPreston PRE | PPPortland Hearts of Pine |
EH E. Hata | In | 2026-08-12 | - | PPPortland Hearts of Pine | PPPortland Hearts of Pine |
DS D. Sing | Out | 2026-08-04 | Return from loan | PPPortland Hearts of Pine | IE Indy Eleven IND |
DS D. Sing | Out | 2026-08-04 | Return from loan | PPPortland Hearts of Pine | IEIndy Eleven IND |
| DSD. Sing | In | 2026-06-30 | Loan | IEIndy Eleven IND | PPPortland Hearts of Pine |
| DSD. Sing | In | 2026-06-30 | Loan | IEIndy Eleven IND | PPPortland Hearts of Pine |
DG D. Gonzalez | In | 2026-05-31 | Loan | HD Houston Dynamo HOU | PPPortland Hearts of Pine |
JD J. Drack | In | 2026-03-31 | - | CB Charleston Battery CHA | PPPortland Hearts of Pine |
AC A. Camara | In | 2026-03-09 | Free agent | PPPortland Hearts of Pine | PPPortland Hearts of Pine |
MK M. Kidd | In | 2026-03-06 | - | SI St. Louis City II | PPPortland Hearts of Pine |
MK M. Kidd | In | 2026-03-06 | - | SISt. Louis City II | PPPortland Hearts of Pine |
DB Diogo Barbosa | In | 2026-03-04 | Free agent | GU Gzira United GIZ | PPPortland Hearts of Pine |
EM Ernest Mensah | In | 2026-02-23 | Free agent | PPPortland Hearts of Pine | PPPortland Hearts of Pine |
AA A. Armour | In | 2026-02-19 | Free agent | CL Crown Legacy | PPPortland Hearts of Pine |
JK J. Keegan | Out | 2026-02-10 | Free agent | PPPortland Hearts of Pine | CC Corpus Christi |
JK J. Keegan | Out | 2026-02-10 | Free agent | PPPortland Hearts of Pine | CCCorpus Christi |
SC S. Coulibaly | Out | 2026-02-05 | Free agent | PPPortland Hearts of Pine | CI Charlotte Independence |
NM N. Messer | Out | 2026-02-04 | Transfer | PPPortland Hearts of Pine | CBCharleston Battery CHA |
KG Konstantinos Georgallides | In | 2026-02-02 | Free agent | — | PPPortland Hearts of Pine |
SW S. Wright | Out | 2026-01-31 | Free agent | PPPortland Hearts of Pine | GF Guadalupe FC BEL |
LK L. Kunga | In | 2026-01-28 | Free agent | UO Union Omaha | PPPortland Hearts of Pine |
NJ N. James | Out | 2026-01-22 | Free agent | PPPortland Hearts of Pine | NT North Texas |
| NJN. James | Out | 2026-01-21 | Free agent | PPPortland Hearts of Pine | NTNorth Texas |
PL P. Langlois | Out | 2026-01-19 | Free agent | PPPortland Hearts of Pine | CCCorpus Christi |
EE E. Espinosa | In | 2026-01-15 | - | PPPortland Hearts of Pine | PPPortland Hearts of Pine |
SV S. Vinberg | Out | 2026-01-12 | Free agent | PPPortland Hearts of Pine | RK Richmond Kickers RIC |
SF S. Faye | In | 2026-01-07 | - | ET Etar Veliko Tarnovo | PPPortland Hearts of Pine |
ZS Z. Scarlett | In | 2025-12-31 | Free agent | CC Carolina Core | PPPortland Hearts of Pine |
| MKM. Kidd | In | 2025-12-31 | - | SISt. Louis City II | PPPortland Hearts of Pine |
ZS Z. Scarlett | In | 2025-12-31 | Free agent | CCCarolina Core | PPPortland Hearts of Pine |
| MKM. Kidd | In | 2025-12-31 | - | SISt. Louis City II | PPPortland Hearts of Pine |
BE B. Evans | In | 2025-12-02 | Free agent | NA Naples | PPPortland Hearts of Pine |
BE B. Evans | In | 2025-12-02 | Free agent | NANaples | PPPortland Hearts of Pine |
| BEB. Evans | In | 2025-12-01 | Free agent | NANaples | PPPortland Hearts of Pine |
CQ Colby Quinones | Out | 2025-11-29 | Free agent | PPPortland Hearts of Pine | — |
ES E. Southern | Out | 2025-11-29 | Free agent | PPPortland Hearts of Pine | — |
AL A. Liadi | Out | 2025-11-29 | Return from loan | PPPortland Hearts of Pine | LE Lexington |
NK N. H. Kvifte | Out | 2025-11-29 | Free agent | PPPortland Hearts of Pine | — |
| SWS. Wright | Out | 2025-11-29 | Free agent | PPPortland Hearts of Pine | GFGuadalupe FC BEL |
MR M. Reilly | Out | 2025-11-29 | Free agent | PPPortland Hearts of Pine | — |
| ESE. Southern | Out | 2025-11-29 | - | PPPortland Hearts of Pine | AC Asheville City |
NK N. Kvifte | In | 2025-07-29 | Free Transfer | AS Asker ASK | PPPortland Hearts of Pine |
| NKN. H. Kvifte | In | 2025-07-28 | Free agent | ASAsker ASK | PPPortland Hearts of Pine |
| NKN. H. Kvifte | In | 2025-07-27 | Free agent | ASAsker ASK | PPPortland Hearts of Pine |
SM S. Mahlamäki | Out | 2025-07-26 | Free Transfer | PPPortland Hearts of Pine | AL Alta ALT |
SM S. Mahlamaki | Out | 2025-07-23 | Free agent | PPPortland Hearts of Pine | ALAlta ALT |
| SMS. Mahlamaki | Out | 2025-07-13 | Free agent | PPPortland Hearts of Pine | ALAlta ALT |
| SCS. Coulibaly | In | 2025-06-30 | Free agent | CH Chateauroux CHA | PPPortland Hearts of Pine |
