[1] Organised by the TT Pro League, part of the proceeds from the game go towards introducing the "Read to Rise" Primary Literacy Program to a school within the winning team's community.

In addition, the winning side also receives TT$10,000 to be donated to a charitable cause of choice.

The inaugural charitable cash prize was given to former captain and player Jan-Michael Williams of W Connection to offset medical expenses for his fiancée Candice Worrell.

Worrell was brutally assaulted while being relieved of her mobile phone in January 2012 and was comatose for nearly three months.

The inaugural match ended with the Savonetta Boys holding the Charity Shield after a 2–0 win over Defence Force on 8 September 2012 at Manny Ramjohn Stadium in Marabella.