Date | Player | Moving from | Moving to | Fee |
000000002008-12-08-00008 December 2008 | Lowe, HowardHoward Lowe | Caledonia AIA | Alpha United FC | Undisclosed[1] |
000000002008-12-08-00008 December 2008 | Johnson, SeanSean Johnson | Tobago United | Alpha United FC | Loan |
000000002008-12-08-00008 December 2008 | Smith, KelvinKelvin Smith | Tobago United | Alpha United FC | Loan |
000000002008-12-10-000010 December 2008 | Beaton, KevinKevin Beaton | Caledonia AIA | Bakewell Topp XX | Undisclosed[2] |
000000002008-12-10-000010 December 2008 | Harris, CareyCarey Harris | Tobago United | Bakewell Topp XX | Loan |
000000002008-12-10-000010 December 2008 | Hercules, CollieCollie Hercules | Tobago United | Bakewell Topp XX | Loan |
000000002008-12-10-000010 December 2008 | McKinnon, KayodeKayode McKinnon | Tobago United | Bakewell Topp XX | Loan |
000000002008-12-10-000010 December 2008 | Reynolds, RichardRichard Reynolds | Tobago United | Bakewell Topp XX | Loan |
000000002008-12-10-000010 December 2008 | Crawford, JavinJavin Crawford | Tobago United | Bakewell Topp XX | Undisclosed |
000000002008-12-10-000010 December 2008 | Isaacs, SelwynSelwyn Isaacs | Tobago United | Bakewell Topp XX | Undisclosed |
000000002008-12-15-000015 December 2008 | Richardson, GregoryGregory Richardson | Joe Public | Pele FC | Loan[3] |
000000002008-12-16-000016 December 2008 | Pollard, CharlesCharles Pollard | Caledonia AIA | Pele FC | Loan[4] |
000000002008-12-21-000021 December 2008 | Joseph, TichardTichard Joseph | Tobago United | Buxton United | Loan[5] |
000000002009-01-09-00009 January 2009 | Lloyd, MiguelMiguel Lloyd | Barcelona FC | W Connection | Free |
000000002009-01-23-000023 January 2009 | Sam, HectorHector Sam | Unattached | San Juan Jabloteh | Free[6] |
000000002009-01-29-000029 January 2009 | Gay, JamalJamal Gay | Joe Public | Rot-Weiß Oberhausen | Undisclosed[7] |
000000002009-02-06-00006 February 2009 | Tinto, HaydenHayden Tinto | Caledonia AIA | Joe Public | Free[8] |
000000002009-02-06-00006 February 2009 | Williams, DauranceDaurance Williams | San Juan Jabloteh | Joe Public | Free |
000000002009-02-06-00006 February 2009 | Woods, MichaelMichael Woods | Caledonia AIA | Joe Public | Free |
000000002009-02-12-000012 February 2009 | Lewis, MicahMicah Lewis | San Juan Jabloteh | Joe Public | Free[9] |
000000002009-02-18-000018 February 2009 | Cooper, SeanSean Cooper | Unattached | Tobago United | Free |
000000002009-02-18-000018 February 2009 | Landeau, JulienJulien Landeau | San Juan Jabloteh | Joe Public | Free[10] |
000000002009-02-18-000018 February 2009 | McKnight, AtibaAtiba McKnight | W Connection | Joe Public | Free |
000000002009-02-18-000018 February 2009 | Parris, AkeemAkeem Parris | United Petrotrin | Joe Public | Free |
000000002009-02-18-000018 February 2009 | Stewart, JohnJohn Stewart | Unattached | Joe Public | Free |
000000002009-02-20-000020 February 2009 | Gray, CydCyd Gray | San Juan Jabloteh | United Petrotrin | Free[11] |
000000002009-02-20-000020 February 2009 | Mason, StokelyStokely Mason | Unattached | United Petrotrin | Free |
000000002009-02-20-000020 February 2009 | Pierre, NigelNigel Pierre | Unattached | United Petrotrin | Free |
000000002009-02-20-000020 February 2009 | Whitley, AurtisAurtis Whitley | W Connection | United Petrotrin | Free |
000000002009-02-23-000023 February 2009 | Villaroel, KevonKevon Villaroel | San Juan Jabloteh | Puerto Rico Islanders | Undisclosed[12] |
000000002009-02-27-000027 February 2009 | Richardson, GregoryGregory Richardson | Joe Public | Toronto FC | Undisclosed[13] |
000000002009-03-11-000011 March 2009 | McAllister, TerrenceTerrence McAllister | Joe Public | Cleveland City Stars | Undisclosed[14] |
000000002009-03-17-000017 March 2009 | Bartholomew, MatthewMatthew Bartholomew | Ferencváros | W Connection | Free[15] |
000000002009-03-17-000017 March 2009 | Downing, AaronAaron Downing | Ferencváros | W Connection | Free |
000000002009-03-17-000017 March 2009 | Wolfe, GlentonGlenton Wolfe | Unattached | W Connection | Free |
000000002009-03-17-000017 March 2009 | Woodley, KevonKevon Woodley | United Petrotrin | W Connection | Free |
000000002009-03-17-000017 March 2009 | Navarro, KerynKeryn Navarro | Unattached | W Connection | Free |
000000002009-03-23-000023 March 2009 | Edwards, KeyonKeyon Edwards | St. Ann's Rangers | Caledonia AIA | Free[16] |
000000002009-03-23-000023 March 2009 | Hernandez, JudahJudah Hernandez | Unattached | Caledonia AIA | Free |
000000002009-03-23-000023 March 2009 | Mussio, KevinKevin Mussio | San Juan Jabloteh | Caledonia AIA | Free |
000000002009-03-23-000023 March 2009 | Smith, ConradConrad Smith | Caledonia AIA | Joe Public | Free |
000000002009-03-30-000030 March 2009 | Noel, TrentTrent Noel | San Juan Jabloteh | United Petrotrin | Undisclosed[17] |
000000002009-04-14-000014 April 2009 | McFarlane, ErrolErrol McFarlane | Al-Mabarrah | St. Ann's Rangers | Free[18] |
000000002009-04-20-000020 April 2009 | Cruickshank, StephenStephen Cruickshank | Ma Pau | Cleveland City Stars | Undisclosed[19] |
000000002009-04-22-000022 April 2009 | Wolfe, AnthonyAnthony Wolfe | Unattached | Ma Pau | Free[20] |
000000002009-04-27-000027 April 2009 | Daniel, NigelNigel Daniel | Unattached | United Petrotrin | Free[21] |
000000002009-05-02-00002 May 2009 | Charles, QuincyQuincy Charles | Ma Pau | Joe Public | Free[22] |
000000002009-05-02-00002 May 2009 | Guevara, AkielAkiel Guevara | Unattached | Joe Public | Free |
000000002009-05-04-00004 May 2009 | Dwarika, ArnoldArnold Dwarika | Joe Public | United Petrotrin | Free[23] |
000000002009-05-04-00004 May 2009 | Glasgow, GaryGary Glasgow | Joe Public | United Petrotrin | Free |
000000002009-05-04-00004 May 2009 | Gray, IanIan Gray | Unattached | United Petrotrin | Free |
000000002009-05-08-00008 May 2009 | Andrews, LyndonLyndon Andrews | Joe Public | Ma Pau | Free |
000000002009-05-08-00008 May 2009 | Noray, KerryKerry Noray | Joe Public | Ma Pau | Free |
000000002009-05-08-00008 May 2009 | Molino, KevinKevin Molino | San Juan Jabloteh | Ma Pau | Loan[24] |
000000002009-05-08-00008 May 2009 | Williams, MekeilMekeil Williams | San Juan Jabloteh | Ma Pau | Loan |
000000002009-05-11-000011 May 2009 | Daniel, KeonKeon Daniel | Unattached | Caledonia AIA | Free[25] |
000000002009-05-18-000018 May 2009 | Glen, CornellCornell Glen | San Juan Jabloteh | San Jose Earthquakes | Undisclosed |
000000002009-06-09-00009 June 2009 | Connell, KevaughnKevaughn Connell | Unattached | San Juan Jabloteh | Free[26] |
000000002009-07-08-00008 July 2009 | Mulraine, TravisTravis Mulraine | Joe Public | San Juan Jabloteh | Undisclosed[27] |
000000002009-07-13-000013 July 2009 | Hoshide, YuYu Hoshide | Northern Virginia Royals | Joe Public | Free[28] |
000000002009-07-16-000016 July 2009 | Williams, Jan-MichaelJan-Michael Williams | Ferencváros | W Connection | Free |
000000002009-07-23-000023 July 2009 | McFarlane, ErrolErrol McFarlane | St. Ann's Rangers | Rochester Rhinos | Undisclosed[29] |
000000002009-07-23-000023 July 2009 | Latapy, RussellRussell Latapy | Unattached | Caledonia AIA | Free[30] |
000000002009-07-27-000027 July 2009 | Rougier, AnthonyAnthony Rougier | Unattached | FC South End | Free[31] |
000000002009-08-04-00004 August 2009 | Noel, TrentTrent Noel | United Petrotrin | Joe Public | Undisclosed[32] |
000000002009-08-04-00004 August 2009 | Joseph, MarcusMarcus Joseph | FC South End | Joe Public | Free |
000000002009-08-04-00004 August 2009 | Cyrus, DaneilDaneil Cyrus | Trinidad and Tobago U20 | Joe Public | Free |
000000002009-08-12-000012 August 2009 | Bangura, AlusineAlusine Bangura | Mighty Blackpool | W Connection | Free[33] |
000000002009-08-14-000014 August 2009 | Aguillera, RomauldRomauld Aguillera | Unattached | W Connection | Free[34] |
000000002009-08-20-000020 August 2009 | Lawrence, DennisDennis Lawrence | Unattached | San Juan Jabloteh | Free[35] |
000000002009-08-24-000024 August 2009 | Jerome, RandolphRandolph Jerome | Pittsburgh Riverhounds | Caledonia AIA | Loan |
000000002009-09-01-00001 September 2009 | Abu Bakr, RadanfahRadanfah Abu Bakr | Caledonia AIA | Swansea City | Loan[36] |
000000002009-09-03-00003 September 2009 | Gullick, LukeLuke Gullick | Chippenham Town | San Juan Jabloteh | Loan[37] |
000000002009-09-13-000013 September 2009 | Wolfe, GlentonGlenton Wolfe | W Connection | San Juan Jabloteh | Free[38] |
000000002009-09-21-000021 September 2009 | Da Costa, MuriloMurilo Da Costa | W Connection | San Juan Jabloteh | Loan |
000000002009-09-22-000022 September 2009 | Diaz, CarlosCarlos Diaz | Ferencváros | W Connection | Free[39] |
000000002009-10-17-000017 October 2009 | Graham, KevinKevin Graham | August Town | Caledonia AIA | Undisclosed[40] |
000000002009-10-17-000017 October 2009 | Stewart, RyanRyan Stewart | Cleveland City Stars | Caledonia AIA | Free |