However, only three clubs from 5 of the 6 regional football associations were awarded qualification into this year's edition, with the Tobago FA as the exception as they only received two.
The lone upset of the round occurred when Joe Public from the Eastern FA Premier Division defeated Club Sando of the National Super League.
In the other all-Pro League fixture, Keyon Edwards scored two late goals to guarantee Caledonia AIA a place in the quarterfinals after a 2–0 victory over Defence Force (PL).
Valtrin United stunned Defence Force (SL) 2–1 with a penalty converted by Matthew Ramirez in the 90th minute.
In the only all-Pro League encounter, Caledonia AIA and Ma Pau ended 1–1 after regulation time following a late equaliser from Stallions' Kerry Daniel in the 90th minute.
The match was contested by Joe Public (PL), who defeated Caledonia AIA 3–1 in their semifinal, and W Connection who beat United Petrotrin 1–0.
Joe Public (PL) used an own goal by Eder Gilmer Arias in the 90th minute to force extra time after the match ended 2–2.
[6] The Eastern Lions then capitalized in the 117th minute when, the tournament's leading scorer with eight goals, Conrad Smith slotted home the winner.