The TT Pro League Golden Boot is an annual Trinidad and Tobago football award given at the beginning of each TT Pro League calendar year to the top goalscorer for the previous season. The Golden Boot has been awarded since the establishment of the Pro League in 1999. The top-scoring Pro League Golden Boot winner is Arnold Dwarika with 45 goals in 28 games during the league's inaugural season. Devorn Jorsling has won the award the most times (4) having scored the most league goals during the 2008, 2010–11, 2012–13, and 2014–15 seasons, all when playing for the Teteron Boys of Defence Force. Jorsling remains the only player to have won the Golden Boot on more than one occasion with his most successful campaigns in 2008, 2012–13, and 2014–15 after leading the league with 21 goals each season.