Jamaica
Premier League (Jamaica) Transfers
Transfer activity in Premier League (Jamaica) 2026/27 — incoming and outgoing deals for clubs in Premier League (Jamaica).
Transfers · 2026/27
108 moves since 1 June 2026. Arrivals and departures for clubs in this league.
Arnett Gardens
Cavalier
Chapelton
Dunbeholden
Harbour View
Humble Lions
Molynes United
Montego Bay United
Mount Pleasant Academy
Racing United
Spanish Town Police
Tivoli Gardens
Treasure Beach
Tru-Juice
Waterhouse| Date | Player | From | To | Type | Fee |
|---|---|---|---|---|---|
| 12 Aug 2026 |  N. Nelson | Molynes United | Mount Pleasant Academy | Free transfer | — |
| 31 Jul 2026 |  D. Petgrave | Cavalier | Cavalier | Transfer | — |
| 31 Jul 2026 |  L. Donaldson | Cavalier | Cavalier | Transfer | — |
| 31 Jul 2026 |  R. Henry |  Portmore United | Portmore United | Transfer | — |
| 30 Jul 2026 |  S. Stein | Cavalier |  Broki | Free transfer | — |
| 28 Jul 2026 |  Nathaniel Francis | Tivoli Gardens | Cavalier | Loan | — |
| 20 Jul 2026 |  Nickalia Fuller | Tivoli Gardens | Mount Pleasant Academy | Free transfer | — |
| 19 Jul 2026 |  D. Smith | Racing United |  Zira | Free transfer | — |
| 17 Jul 2026 |  R. Thomas | Arnett Gardens | Mount Pleasant Academy | Free transfer | — |
| 17 Jul 2026 |  R. Wright |  Lernayin Artsakh | Cavalier | - | — |
| 30 Jun 2026 |  Nicholas Hamilton | Waterhouse | Cavalier | - | — |
| 30 Jun 2026 |  T. Reid | Harbour View | Mount Pleasant Academy | - | — |
| 29 Jun 2026 |  J. Frazer | Molynes United | Cavalier | Loan | — |
| 29 Jun 2026 |  K. Wilson | Arnett Gardens | Mount Pleasant Academy | Loan | — |
| 29 Jun 2026 |  M. Ellis | Molynes United | Cavalier | Loan | — |
| 04 May 2026 |  Orane Watson | Chapelton | Portmore United | - | — |
| 16 Apr 2026 |  T. Magee | Mount Pleasant Academy |  Colorado Springs | Free transfer | — |
| 12 Apr 2026 |  K. Caull |  Europa Point | Montego Bay United | Free transfer | — |
| 23 Mar 2026 |  C. Burke |  Lexington | Portmore United | Free transfer | — |
| 22 Mar 2026 |  D. Smith | Mount Pleasant Academy | Mount Pleasant Academy | - | — |
| 27 Feb 2026 |  Odane Nish | Montego Bay United | Racing United | Free transfer | — |
| 23 Feb 2026 |  J. Barclay | Portmore United |  St. Louis City II | - | — |
| 22 Feb 2026 |  S. Taylor | Mount Pleasant Academy | Mount Pleasant Academy | - | — |
| 08 Feb 2026 |  J. Fletcher | Montego Bay United |  Hai Phong | Transfer | — |
| 03 Feb 2026 |  Peterson Pierre-Louis | Real Hope | Mount Pleasant Academy | Free transfer | — |
| 31 Jan 2026 |  O. Miller | Portmore United | Portmore United | Free transfer | — |
| 30 Jan 2026 |  C. Daley |  FK Rabotnicki | Mount Pleasant Academy | Free transfer | — |
| 29 Jan 2026 |  Tevin Shaw | Mount Pleasant Academy | Arnett Gardens | Free transfer | — |
| 28 Jan 2026 |  D. Mckenzie | Cavalier | Chapelton | Transfer | — |
| 24 Jan 2026 |  George Headley | Portmore United | Harbour View | - | — |
| 22 Jan 2026 |  Dyllan John | Waterhouse |  Carolina Core | - | — |
| 18 Jan 2026 |  K. Gordon | Cavalier | Cavalier | - | — |
| 14 Jan 2026 | K. Wilson | Mount Pleasant Academy | Arnett Gardens | Loan | — |
| 11 Jan 2026 |  J. Mcgregor | Portmore United | Spanish Town Police | - | — |
| 31 Dec 2025 |  D. Cohen | Vere United | Portmore United | Free transfer | — |
| 31 Dec 2025 |  Kimani Arbourine | Arnett Gardens | Montego Bay United | Free transfer | — |
| 31 Dec 2025 |  P. McGregor | Molynes United | Portmore United | Free transfer | — |
| 31 Dec 2025 |  T. Lynch | Mount Pleasant Academy | Cavalier | Free transfer | — |
| 30 Dec 2025 |  D. Hutchinson |  New England Revolution | Racing United | Free transfer | — |
| 30 Dec 2025 |  D. Miller | Cavalier | Treasure Beach | - | — |
| 03 Dec 2025 |  Cardel Benbow | Portmore United | Waterhouse | Free transfer | — |
| 29 Nov 2025 |  Tyrone Harrison | Montego Bay United | Harbour View | - | — |
| 04 Oct 2025 | T. Magee | Vere United | Mount Pleasant Academy | Free transfer | — |
| 29 Sept 2025 |  Wisdom Ubani |  Ikorodu City | Molynes United | Free transfer | — |
| 03 Sept 2025 |  P. Vassell | Montego Bay United |  Birmingham Legion | Free transfer | — |
| 01 Sept 2025 |  J. Lynch | Portmore United | Đại Học Văn Hiến | Transfer | — |
| 31 Aug 2025 |  Romarion Thomas | Vere United | Cavalier | Free transfer | — |
| 30 Aug 2025 |  A. Bennett | Harbour View | Arnett Gardens | Transfer | — |
| 29 Aug 2025 |  M. Allen | Chapelton | Dunbeholden | Free transfer | — |
| 27 Aug 2025 |  Zhaine Pinnock | Portmore United | Chapelton | - | — |
| 23 Aug 2025 |  D. Thomas | Dunbeholden | Racing United | Free transfer | — |
| 23 Aug 2025 | J. Frazer | Cavalier | Molynes United | Transfer | — |
| 23 Aug 2025 |  J. Morgan | Cavalier | Molynes United | Transfer | — |
| 22 Aug 2025 |  R. Ramsey | Humble Lions | Montego Bay United | Free transfer | — |
| 21 Aug 2025 |  C. Murray | Harbour View | Waterhouse | Transfer | — |
| 20 Aug 2025 |  Jahmari Clarke |  Yeovil Town | Montego Bay United | Free transfer | — |
| 19 Aug 2025 |  D. Phillips | Montego Bay United | Mount Pleasant Academy | Transfer | — |
| 19 Aug 2025 |  G. Tomlinson | Chapelton | Cavalier | Transfer | — |
| 19 Aug 2025 |  K. Foster | Waterhouse | Mount Pleasant Academy | Free transfer | — |
| 19 Aug 2025 |  Odean Pennycooke | Mount Pleasant Academy | Dunbeholden | Free transfer | — |
| 19 Aug 2025 |  R. Biggs | Racing United | Mount Pleasant Academy | Free transfer | — |
| 18 Aug 2025 |  K. Graham | Mount Pleasant Academy | Chapelton | Free transfer | — |
| 16 Aug 2025 |  Kaïlé Auvray | Cavalier |  Columbus Crew II | - | — |
| 15 Aug 2025 | Kaïlé Auvray | Cavalier | Auvray Kaile | Free transfer | — |
| 14 Aug 2025 |  D. Massicot |  Grenades | Cavalier | Free transfer | — |
| 12 Aug 2025 |  K. McGregor | Harbour View | Treasure Beach | Free transfer | — |
| 12 Aug 2025 | M. Ellis | Cavalier | Molynes United | Loan | — |
| 11 Aug 2025 |  K. McGregor | Arnett Gardens | Treasure Beach | Loan | — |
| 10 Aug 2025 |  Matthew Woo Ling | Vere United | Montego Bay United | Free transfer | — |
| 09 Aug 2025 | N. Nelson | Mount Pleasant Academy | Dunbeholden | Free transfer | — |
| 07 Aug 2025 |  D. Atkinson | Cavalier |  Rhode Island | Free transfer | — |
| 06 Aug 2025 |  Okeemo Jones | Harbour View | Montego Bay United | Transfer | — |
| 06 Aug 2025 |  T. Lewis | Harbour View | Montego Bay United | Free transfer | — |
| 04 Aug 2025 |  N. Blair | Waterhouse | Cavalier | Transfer | — |
| 03 Aug 2025 |  M. Reid | Phoenix FA | Portmore United | Free transfer | — |
| 03 Aug 2025 |  Navardo Blair | Waterhouse | Cavalier | Free transfer | — |
| 30 Jul 2025 |  Jermie Lynch | Portmore United |  Văn Hiến | Free transfer | — |
| 28 Jul 2025 |  P. McGregor | Molynes United | Portmore United | Free transfer | — |
| 24 Jul 2025 |  J. Smith | Cavalier | Arnett Gardens | Transfer | — |
| 24 Jul 2025 |  W. Brown | Arnett Gardens | Mount Pleasant Academy | Free transfer | — |
| 23 Jul 2025 |  Daniel Saint-Fleur | Real Hope | Mount Pleasant Academy | Free transfer | — |
| 23 Jul 2025 |  R. Intervil | Real Hope | Mount Pleasant Academy | Free transfer | — |
| 23 Jul 2025 |  R. White |  Vere United | Arnett Gardens | Transfer | — |
| 22 Jul 2025 |  J. Calvin | Cavalier |  ST Mirren | Free transfer | — |
| 21 Jul 2025 |  Revaldo Mitchell | FK Rabotnicki | Waterhouse | Free transfer | — |
| 14 Jul 2025 |  A. Johnson | Dunbeholden | Waterhouse | Free transfer | — |
| 01 Jul 2025 | A. Johnson | Chapelton | Dunbeholden | Loan | — |
| 01 Jul 2025 |  C. Benny | Montego Bay United |  Athletic Club | Free transfer | — |
| 01 Jul 2025 |  D. Miller | Cavalier | Treasure Beach | Free transfer | — |
| 01 Jul 2025 | D. Phillips | Montego Bay United | Mount Pleasant Academy | Free transfer | — |
| 01 Jul 2025 |  J. Morrison | Humble Lions | Portmore United | — | — |
| 01 Jul 2025 | K. Graham | Humble Lions | Mount Pleasant Academy | Loan | — |
| 01 Jul 2025 |  K. Thompson | Molynes United | Cavalier | Loan | — |
| 01 Jul 2025 | M. Ellis | Humble Lions | Cavalier | Loan | — |
| 01 Jul 2025 |  O. Brown | Racing United | Arnett Gardens | Loan | — |
| 01 Jul 2025 |  R. King | Cavalier | ST Mirren | Free transfer | — |
| 01 Jul 2025 | W. Brown | Arnett Gardens | Mount Pleasant Academy | Transfer | — |
| 30 Jun 2025 | D. Mckenzie | Vere United | Cavalier | Free transfer | — |
| 30 Jun 2025 |  D. Merrick | Dunbeholden | Montego Bay United | - | — |
| 30 Jun 2025 | K. Foster | Waterhouse | Mount Pleasant Academy | - | — |
| 30 Jun 2025 | K. Wilson | Harbour View | Mount Pleasant Academy | Free transfer | — |
| 30 Jun 2025 |  Michael Forbes | Vere United | Cavalier | Free transfer | — |
| 30 Jun 2025 | R. Biggs | Racing United | Mount Pleasant Academy | Free transfer | — |
| 29 Jun 2025 | D. Merrick | Mount Pleasant Academy | Dunbeholden | - | — |
| 29 Jun 2025 |  J. Dunn | Cavalier | Tivoli Gardens | Loan | — |
| 29 Jun 2025 |  J. White | Cavalier |  Hereford | - | — |
| 29 Jun 2025 |  Junior Turner Nevaughn | Montego Bay United | Dunbeholden | Free transfer | — |
| 29 Jun 2025 | K. McGregor | Harbour View | Arnett Gardens | Loan | — |