Every team based on the island of Trinidad took part in the tournament, with Tobago United as the lone Pro League representative that did not participate.
The bottom four teams in the table, United Petrotrin, FC South End, St. Ann's Rangers, and Police entered the tournament in the qualifying round.
On 17 November, St. Ann's Rangers pulled an upset over FC South End 1–0 with Josimar Belgrave providing the lone goal.
[3] In the quarterfinals on 20 November, Joe Public used four goals from 2009 Golden Boot winner, Kerry Baptiste, to a 9–1 win against Police.
On the other side of the bracket, Caledonia AIA defeated St. Ann's Rangers by a score 5–0 following a hat-trick from Kendall Velox, while Defence Force provided the closest match in the round with their win over San Juan Jabloteh 2–1.