As the Morvant/Laventille Stallions entered the competition as the defending league cup winners they were the first to draw from eight secretly numbered cards respective to spots in the quarterfinal round.
Caledonia AIA's Kareem Joseph was immediately followed by T&TEC midfielder Keeron Benito who drew the card that pitted the Electricity Boys against the defending champion at Hasely Crawford Stadium.
The quarterfinal round began with a stunning upset from St. Ann's Rangers defeating North East Stars 2–1 in the cup opener.
[3][4] In addition, Defence Force ousted Pro League newcomer Central FC 3–0 with goals from the Army's new strike partnership Ro-Jo consisting of Richard Roy and Devorn Jorsling.
[8] The Teteron Boys returned to the final for the first time since 2010 with a pair of goals from Trinidad and Tobago international players Jerwyn Balthazar and Kevon Carter.