[2] The automatic quarterfinal qualifiers in order of league position were: Defence Force, Joe Public, W Connection, Ma Pau, San Juan Jabloteh, and Caledonia AIA.
The tournament commenced on 23 July with FC South End defeating Police 5–3 in a penalty shootout to determine the tenth team to enter the competition.
[3] In the qualifying round, North East Stars took an early lead over FC South End with a strike from Sean Fraser and eased into the quarterfinals by a 3–0 score.
[3] In the other fixture, St. Ann's Rangers and Tobago United needed 16 penalty kicks to determine the winner after the match ended scoreless.
[9] On 13 August, North East Stars captured the title with the lone goal supplied by Sean Fraser in the 1–0 win over San Juan Jabloteh at Marvin Lee Stadium in Macoya.