[1] W Connection entered as the Pro Bowl holders, having defeated North East Stars 4–3 in a penalty shootout after the match ended in 0–0 in regulation during the 2013 final at Hasely Crawford Stadium.
[2][3] The competition commenced on 2 May with all nine Pro League teams competing in single elimination beginning with the qualifying round and concluded on 23 May with the final.
The lowest two teams in the league table, San Juan Jabloteh and St. Ann's Rangers, were drawn into the qualifying round, which was held on 2 May 2014 at the Ato Boldon Stadium in Couva.
[4] W Connection entered the competition as the defending Pro Bowl winners and were drawn against Caledonia AIA in the later quarterfinal match-up at Hasely Crawford Stadium.
The final quarterfinal match, also held at the Ato Boldon Stadium, North East Stars will face recently crowned 2014 Lucozade Sport Goal Shield winners Central FC.