Portmore United: every transfer in and out, fees paid and earned, squad market value.
| Date | Player | From | To | Fee |
|---|---|---|---|---|
| 2025-08-23 | Benjamin Williams | Portmore United | Harbour View FC | Free |
| 2024-07-01 | Romario Guthrie | Mount Pleasant | Portmore United | — |
| 2022-01-01 | Kemar Foster | Portmore United | Waterhouse | — |
| 2021-01-01 | Demario Phillips | Dunbeholden FC | Portmore United | Loan |
| 2018-07-01 | Demario Phillips | Portmore United | Sanjaxx Lions | — |
| 2018-01-01 | Sue-Lae McCalla | Portmore United | Humble Lions | — |
| 2016-01-01 | Sue-Lae McCalla | Portmore United | Cavalier SC | Loan |
| 2016-01-01 | Kevon Lambert | Portmore United | Montego Bay Utd | — |
| 2015-01-01 | Alvas Powell | Portmore United | Portland | — |
| 2013-07-01 | Alvas Powell | Portmore United | Portland | Loan |
| 2011-07-01 | Kemar Foster | Frazier's Whip | Portmore United | — |