Trinidad and Tobago Charity Shield
The Trinidad and Tobago Charity Shield, now officially the Digicel Charity Shield, is TT’s annual football super cup. It features the previous season’s TT Pro League champions against the Pro Bowl winners. If the same team wins both, the league runners-up take the other spot.
The match is organized by the TT Pro League and is sponsored by Digicel. It’s often described as a “glorified friendly” and sits below the FA Trophy and First Citizens Cup, but it is a recognized super cup. Proceeds help the Read to Rise primary literacy program, and the winning team receives TT$10,000 to donate to a charity of its choice.
The first game was played in 2012 to start the 2012–13 season. It was W Connection (2011–12 Pro League champions) vs Defence Force (Pro Bowl winners). W Connection won 2–0 on 8 September 2012 at Manny Ramjohn Stadium in Marabella. The inaugural charitable prize went to Jan-Michael Williams of W Connection to help with medical expenses for his fiancée Candice Worrell, who had been severely injured in an assault.
In 2013, W Connection won again, beating Defence Force 4–2 at Hasely Crawford Stadium. They secured a third straight title in 2014.
Current champions: W Connection (4th title). Most championships: W Connection (4 titles).
This page was last edited on 3 February 2026, at 09:17 (CET).