Results
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.
Qualifying round
The competition kicked off with the qualifying round between the San Juan Jabloteh and St. Ann's Rangers, which represented the bottom of the 2013–14 TT Pro League league table. The San Juan Kings used goals on either side of the half from Jean-Luc Rochford and Micah Lewis, respectively, to advance to the quarterfinals to face W Connection.[4][5]
| 2 April 2014 | San Juan Jabloteh | 2–0 | St. Ann's Rangers | Malabar, Trinidad |
| 18:00 (UTC-4) | Rochford  5'Lewis 61' |
Report | Stadium: Larry Gomes Stadium |
Quarterfinals
In the quarterfinals, all four of the higher seeds progressed. In the early match in Couva on 4 April, Central FC easily defeated the Stallions of Morvant/Laventille with a 4–0 win, which included a first-half brace from Willis Plaza.[6] However, the Akini Adams stole the spotlight in the late match between Point Fortin Civic and Defence Force. Acting as a stand-in goalkeeper, Adams saved two kicks in the penalty shootout, after the match ended 1–1, to help Point Fortin advance to the semifinals.[7] After the match, Adams dedicated the win to his brother Akeem Adams, who died on 30 December 2013 from a heart attack suffered in September while playing for Ferencváros in Hungary.[8] The following day, W Connection won convincingly over San Juan Jabloteh after scoring three goals in the first half.[9] North East Stars used a brace from Keron Cummings to upend Police and advance to the semifinals.[10]
| 4 April 2014 | Central FC | 4–0 | Caledonia AIA | Couva, Trinidad |
| 18:00 (UTC-4) | Plaza 14' (pen.), 43' Guerra 81'Oliver 90' (pen.) |
Report | Stadium: Ato Boldon Stadium Referee: Mervyn Wallace |
| 4 April 2014 | Point Fortin Civic | 1–1 (4–3 p) | Defence Force | Couva, Trinidad |
| 20:00 (UTC-4) | Report | Stadium: Ato Boldon Stadium Referee: Cecil Hinds | ||
| Penalties | ||||
M. Joseph  Toussaint Ettienne Bass |
Jorsling Roy Gonzales  Russell Jr. Rivers |
|||
| 5 April 2014 | W Connection | 3–1 | San Juan Jabloteh | Couva, Trinidad |
| 18:00 (UTC-4) | Paul 8' Clarence 15'Arcia 24' |
Report | Smith 75' |
Stadium: Ato Boldon Stadium Referee: Gyasi McDonald |
| 5 April 2014 | North East Stars | 2–1 | Police | Couva, Trinidad |
| 20:00 (UTC-4) | Cummings 2', 41' |
Report | Perry 72' |
Stadium: Ato Boldon Stadium Referee: Neal Brizan |
Semifinals
On 11 April, W Connection and Central FC won their semifinal contests to advance to the final on 25 April at Ato Boldon Stadium in Couva. In the first semifinal, Central FC defeated North East Stars 2–0 following goals from their two young strikers; Dwight Quintero and Rundell Winchester on either side of half-time.[11] W Connection used a lone goal from Hashim Arcia in the 53rd minute to defeat Point Fortin Civic 1–0.[11]
| 11 April 2014 | Central FC | 2–0 | North East Stars | Couva, Trinidad |
| 18:00 (UTC-4) | Quintero 15' Winchester 79' |
Report | Stadium: Ato Boldon Stadium Referee: Gyasi McDonald |
| 11 April 2014 | W Connection | 1–0 | Point Fortin Civic | Couva, Trinidad |
| 20:00 (UTC-4) | Arcia 53' |
Report | Stadium: Ato Boldon Stadium Referee: Rodphin Harris |
Final
In the final on 25 April, Central FC scored two goals in succession from Rundell Winchester and Marvin Oliver to power the Couva Sharks to their first Goal Shield title.[12] For his performance in the final, Winchester was named the Most Valuable Player after providing his second goal of the tournament and setting up the winning goal from Oliver.[13]
| 25 April 2014 | W Connection | 1–2 | Central FC | Couva, Trinidad |
| 20:00 (UTC-4) | A. Jones 21' |
Report | Winchester 13' Oliver 19' |
Stadium: Ato Boldon Stadium Referee: Neal Brizan |