The 2014 Trinidad and Tobago Goal Shield was the fifth season of the Lucozade Sport Goal Shield, which is a knockout tournament competition for Trinidad and Tobago teams competing in the TT Pro League. W Connection entered as the cup holders having defeated North East Stars 4–3 in a penalty shootout in the 2013 final. Continuing from previous seasons, the competition not only allowed the winner and runner-up healthy purses at the end of the tournament, but more so give an added incentive for more goals to be scored throughout the tournament. In particular, the winner of the competition was awarded TT$30,000 plus an additional TT$3,000 for every goal scored in the final, TT$2,000 for every goal in the semifinals, and TT$1,000 for each goal scored in the quarterfinals. Whereas, the runner-up was awarded TT$10,000 plus TT$1,500 for every goal scored in the final, TT$1,000 for every goal in the semifinals, and TT$500 for each goal scored in the quarterfinals.

Since the league expanded to nine clubs for the 2013–14 TT Pro League season, the competition re-introduced the qualifying round to narrow the number of teams prior to the quarterfinals. Seeding was determined from the league standings at the end of fixtures held on 29 March 2014.W Connection entered the competition as the league leader and top seeded team in the competition. 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 draw for the quarterfinals took place on 31 March 2014 at the Capital Plaza in Port of Spain. 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.

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