For the second consecutive season, all eight teams competing in the TT Pro League entered the competition at the quarterfinal round. The draw for the quarterfinals took place on 15 May 2013 at the Digicel corporate box in Queen's Park Oval in Port of Spain. Defence Force entered the competition as the defending Pro Bowl winners and were the first to draw from eight secretly numbered cards respective to spots in the quarterfinal round. Following the draw, quarterfinal match-ups resulted in Defence Force facing T&TEC who finished last following the Pro League season. In the later quarterfinal match-up saw North East Stars facing St. Ann's Rangers. However, the match-up of the round will contest Caledonia AIA and W Connection at Manny Ramjohn Stadium in Couva. The two clubs finished second and third, respectively, in the league table. The other quarterfinal match-up in Couva resulted Central FC facing Police.
Schedule
The schedule for the 2013 Digicel Pro Bowl, as announced by the TT Pro League:
All matches were played for 90 minutes duration, at the end of which if the match was still tied, penalty-kicks were used to determine the match winner.
Quarterfinals
In the quarterfinals on 17 May, Defence Force advanced to the semifinals with a win over T&TEC 5–0. The Teteron Boys scored all five goals in the second half and used a hat-trick from Kevon Carter. North East Stars recorded a clean sheet over St. Ann's Rangers with goals from Kennedy Hinkson, Marcus Gomez, and Kareem Moses. Peter Byers was the lone goal scorer in a 1–0 win for Central FC over Police. In the match-up of the round, W Connection ousted Caledonia AIA from the competition 3–1 at Ato Boldon Stadium in Couva. ---- ---- ---- ----
Semifinals
In the semifinals, on 24 May, W Connection upended the recently crowned Pro League champions Defence Force 4–3 in a penalty shoot-out after the match ended in a 1–1 draw. Andrei Pacheco scored his second goal in as many matches to give the Savonetta Boys a 1–0 lead in the eighth minute. However, the match remained level until a Devorn Jorsling goal in the 74th to send the match into penalties. Alejandro Figueroa saved two penalties from Richard Roy and Kevon Carter to give W Connection the victory and trip to the final. The other semifinal match would also need a penalty shoot-out to determine the winner. North East Stars used a 5–3 win on penalties to end Central FC's inaugural season. The Sangre Grande Boys claimed the lead in the 57th minute with a goal from Kennedy Hinkson. However, one minute later the Sharks equalised through Rundell Winchester. The match ended in a 1–1 draw and resulted in penalties. Cleon John denied Darren Mitchell in the third round of spot kicks to give North East Stars the win after the club successfully converted five consecutive penalties. ---- ----
Final
On 29 May, W Connection claimed their third Digicel Pro Bowl title following a 4–3 penalty shoot-out win over North East Stars after a scoreless draw. The Pro Bowl title was the Savonetta Boys third and first in six years. Colombian goalkeeper Alejandro Figueroa saved the first penalty in the shoot-out from Cornell Glen. However, Joevin Jones missed on his attempt to keep the shoot-out level. Afterwards, Elijah Manners and Kareem Moses converted for North East Stars, as well as Silvio Spann and Gerard Williams for W Connection. The momentum shifted after Elton John hit his penalty off the crossbar. After Hashim Arcia and Kennedy Hinkson scored their shots for W Connection and North East Stars respectively, W Connection captain and Saint LucianinternationalElijah Joseph hit his penalty down the center past Cleon John to give the Savonetta Boys the win.
