The prize money for the winner, as announced by TT Pro League CEO Dexter Skeene, is determined by the players, the clubs and the communities.

The prize money will be the amount received from gate receipts and TT$100,000, courtesy of tournament sponsors Digicel.

In fact, the Savonetta Boys are the current holders of the Pro Bowl after defeating North East Stars 4–3 in a penalty shoot-out in 2013 after the match ended in a scoreless draw,[3] and winning again in 2014.

The San Juan Kings secured the Pro Bowl title in consecutive seasons in 2005 and 2006 over their rivals.

[6] The Eastern Lions repeated as winners in 2011 before shortly afterwards withdrawing from the TT Pro League.

[7] The competition is open to all clubs in the TT Pro League and is divided into three rounds consisting of single-legged matches.