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The TT Pro League awards is an annual awards ceremony commemorating football-related people, given at the conclusion of each TT Pro League season since its inauguration in 1999. The ceremony is held prior to the opening match of the following Pro League season. In addition to the annual Golden Boot recipient, the awards ceremony honours the Player, Manager, Referee, Assistant Referee, and Match Commissioner of the previous season. Beginning in 2005, the Pro League has also recognised the best position players of each season. The individual recipients are awarded Best Goalkeeper, Defender, Midfielder, and Forward. There are only two team award recipients each year: Best Team and Most Disciplined Team of the Year.[1][2]
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| 1999 awards | |||
|---|---|---|---|
| Award | Winner | ||
| Player of the Year |  Arnold Dwarika (Joe Public) | ||
| Manager of the Year | Unknown | ||
| Golden Boot | Arnold Dwarika (Joe Public) | ||
| Team of the Year | Joe Public[3] | ||
| Most Disciplined Team of the Year | W Connection | ||
| Referee of the Year | Ramesh Ramdhan | ||
| Assistant Referee of the Year | Haseeb Mohammed | ||
| Match Commissioner of the Year | Unknown | ||
| 2000 awards | |||
|---|---|---|---|
| Award | Winner | ||
| Player of the Year | Reynold Carrington (W Connection) | ||
| Manager of the Year |  Stuart Charles-Fevrier (W Connection) | ||
| Golden Boot | Jason Scotland (Defence Force) | ||
| Team of the Year | W Connection | ||
| Most Disciplined Team of the Year | W Connection | ||
| Referee of the Year | Noel Bynoe | ||
| Assistant Referee of the Year | Michael Ragoonath | ||
| Match Commissioner of the Year | Norris Ferguson | ||
| 2001 awards | |||
|---|---|---|---|
| Award | Winner | ||
| Player of the Year | Unknown | ||
| Manager of the Year | Stuart Charles-Fevrier (W Connection) | ||
| Golden Boot | Unknown | ||
| Team of the Year | Unknown | ||
| Most Disciplined Team of the Year | Unknown | ||
| Referee of the Year | Unknown | ||
| Assistant Referee of the Year | Unknown | ||
| Match Commissioner of the Year | Unknown | ||
| 2002 awards | |||
|---|---|---|---|
| Award | Winner | ||
| Player of the Year | Andre Toussaint (Joe Public)[4] | ||
| Manager of the Year | Stuart Charles-Fevrier (W Connection)[5] | ||
| Golden Boot | Sean Julien (South Starworld Strikers) | ||
| Team of the Year | W Connection[4] | ||
| Most Disciplined Team of the Year | South Starworld Strikers[4] | ||
| Referee of the Year | Unknown | ||
| Assistant Referee of the Year | Unknown | ||
| Match Commissioner of the Year | Unknown | ||
| 2003–04 awards | |||
|---|---|---|---|
| Award | Winner | ||
| Player of the Year |  Charles Pollard (North East Stars)[6] | ||
| Manager of the Year |  Ricky Hill (San Juan Jabloteh)[7] | ||
| Golden Boot | Randolph Jerome (North East Stars) | ||
| Team of the Year | North East Stars | ||
| Most Disciplined Team of the Year | Unknown | ||
| Referee of the Year | Unknown | ||
| Assistant Referee of the Year | Unknown | ||
| Match Commissioner of the Year | Unknown | ||
| 2004 awards | |||
|---|---|---|---|
| Award | Winner | ||
| Player of the Year | Jerren Nixon (North East Stars)[8] | ||
| Manager of the Year | James McLean (North East Stars)[9] | ||
| Golden Boot | Jerren Nixon (North East Stars) | ||
| Team of the Year | W Connection[10] | ||
| Most Disciplined Team of the Year | Tobago United[11] | ||
| Referee of the Year | Unknown | ||
| Assistant Referee of the Year | Unknown | ||
| Match Commissioner of the Year | Unknown | ||
| 2005 awards | |||
|---|---|---|---|
| Award | Winner | ||
| Player of the Year |  Gefferson (W Connection)[12] | ||
| Manager of the Year | Brian Williams (United Petrotrin)[13] | ||
| Golden Boot | Gefferson (W Connection) | ||
| Earl Jean (W Connection) | |||
| Team of the Year | W Connection[12] | ||
| Most Disciplined Team of the Year | W Connection[12] | ||
| Referee of the Year | Neal Brizan | ||
| Assistant Referee of the Year | Joseph Taylor | ||
| Match Commissioner of the Year | Wayne Caesar | ||
| 2006 awards | |||
|---|---|---|---|
| Award | Winner | ||
| Player of the Year | Jan-Michael Williams (W Connection)[14] | ||
| Manager of the Year | Michael McComie (Joe Public) | ||
| Best Goalkeeper | Jan-Michael Williams (W Connection) | ||
| Best Defender | Sheldon Emmanuel (Caledonia AIA) | ||
| Best Midfielder | William Oliveira (W Connection) | ||
| Best Forward |  Roen Nelson (Joe Public) | ||
| Golden Boot | Roen Nelson (Joe Public) | ||
| Anthony Wolfe (San Juan Jabloteh) | |||
| Team of the Year | San Juan Jabloteh | ||
| Most Disciplined Team of the Year | W Connection | ||
| Referee of the Year | Shane de Silva | ||
| Assistant Referee of the Year | Lyndon Burton | ||
| Match Commissioner of the Year | Wayne Caesar | ||
| 2007 awards | |||
|---|---|---|---|
| Award | Winner | ||
| Player of the Year | Marvin Oliver (Caledonia AIA)[15] | ||
| Manager of the Year | Stuart Charles-Fevrier (W Connection) | ||
| Best Goalkeeper | Cleon John (San Juan Jabloteh)[16] | ||
| Best Defender | Elijah Joseph (W Connection) | ||
| Best Midfielder | Marvin Oliver (Caledonia AIA)[17] | ||
| Best Forward |  Peter Byers (San Juan Jabloteh) | ||
| Golden Boot | Peter Byers (San Juan Jabloteh) | ||
| Team of the Year | W Connection | ||
| Most Disciplined Team of the Year | W Connection | ||
| Referee of the Year | Neal Brizan | ||
| Assistant Referee of the Year | Joseph Taylor | ||
| Match Commissioner of the Year | Norris Ferguson | ||
| 2008 awards | |||
|---|---|---|---|
| Award | Winner | ||
| Player of the Year | Trent Noel (San Juan Jabloteh)[18] | ||
| Manager of the Year | Terry Fenwick (San Juan Jabloteh) | ||
| Golden Boot | Devorn Jorsling (Defence Force) | ||
| Team of the Year | San Juan Jabloteh | ||
| Most Disciplined Team of the Year | North East Stars | ||
| Referee of the Year | Neal Brizan | ||
| Assistant Referee of the Year | Joseph Pierre | ||
| Match Commissioner of the Year | Boris Punch | ||
| 2009 awards | |||
|---|---|---|---|
| Award | Winner | ||
| Player of the Year | Kerry Baptiste (Joe Public)[19] | ||
| Manager of the Year | Derek King (Joe Public)[20] | ||
| Best Goalkeeper |  Alejandro Figueroa (Joe Public) | ||
| Best Defender | Keyeno Thomas (Joe Public) | ||
| Best Midfielder | Trent Noel (Joe Public) | ||
| Best Forward | Kerry Baptiste (Joe Public) | ||
| Golden Boot | Kerry Baptiste (Joe Public) | ||
| Team of the Year | Joe Public[21] | ||
| Most Disciplined Team of the Year | Caledonia AIA | ||
| Referee of the Year | Neal Brizan | ||
| Assistant Referee of the Year | Ainsley Rochard | ||
| Match Commissioner of the Year | Boris Punch | ||
| 2010–11 awards | |||
|---|---|---|---|
| Award | Winner | ||
| Player of the Year | Devorn Jorsling (Defence Force)[22] | ||
| Manager of the Year | Ross Russell (Defence Force) | ||
| Best Goalkeeper | Cleon John (San Juan Jabloteh) | ||
| Best Defender | Corneal Thomas (Ma Pau) | ||
| Best Midfielder | Trent Noel (Joe Public) | ||
| Best Forward | Devorn Jorsling (Defence Force) | ||
| Golden Boot | Devorn Jorsling (Defence Force) | ||
| Team of the Year | Defence Force | ||
| Most Disciplined Team of the Year | St. Ann's Rangers | ||
| Referee of the Year | Neal Brizan | ||
| Assistant Referee of the Year | Dion Neil | ||
| Match Commissioner of the Year | Norris Ferguson | ||
| 2011–12 awards | |||
|---|---|---|---|
| Award | Winner | ||
| Player of the Year | Richard Roy (Defence Force)[22] | ||
| Manager of the Year | Jamaal Shabazz (Caledonia AIA) | ||
| Best Goalkeeper | Jan-Michael Williams (W Connection) | ||
| Best Defender | Nuru Abdullah Muhammad (Caledonia AIA) | ||
| Best Midfielder | Ataullah Guerra (Caledonia AIA) | ||
| Best Forward | Richard Roy (Defence Force) | ||
| Golden Boot | Richard Roy (Defence Force) | ||
| Team of the Year | Caledonia AIA | ||
| Most Disciplined Team of the Year | W Connection | ||
| Referee of the Year | Neal Brizan | ||
| Assistant Referee of the Year | Cindy Mohammed | ||
| Match Commissioner of the Year | Boris Punch | ||
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| Rank | Club | Total |
|---|---|---|
1 |
W Connection | 24 |
2 |
Joe Public | 16 |
3 |
Defence Force | 10 |
| San Juan Jabloteh | 10 | |
5 |
Morvant Caledonia United | 8 |
6 |
North East Stars | 7 |
7 |
South Starworld Strikers | 2 |
8 |
Ma Pau | 1 |
| St. Ann's Rangers | 1 | |
| Tobago United | 1 | |
| United Petrotrin | 1 | |
| Total | 81 | |
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