2014 Trinidad and Tobago Goal Shield

The remaining top seeds were Central FC, North East Stars, and Point Fortin Civic after placing second, third, and fourth, respectively, in the league table at the time of the draw.

The quarterfinal matches to be played on 4 April in Ato Boldon Stadium resulted in Central FC facing Caledonia AIA and Point Fortin Civic against Defence Force.

The following night in Couva, W Connection will face the winner of the qualifying round between the bottom two in the league table, San Juan Jabloteh and St. Ann's Rangers, and North East Stars against Police.

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.

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.