[5] In the only match-up between teams from the Pro League, San Juan Jabloteh defeated defending champions Joe Public 2–0 after extra time to secure their place in the quarterfinals.
[6] Caledonia AIA received a scare from Defence Force from the National Super League, but prevailed using a 111th-minute goal from Ishmael Daniel in extra time.
The lowest ranked team left in the competition was La Brea All-Stars of the Southern FA Premier Division, the third tier of Trinidad and Tobago football.
La Brea All-Stars of the SFA Premier Division were defeated by San Juan Jabloteh 5–0 in the late match at Ato Boldon Stadium.
[7] The other potential giant-killer Joe Public from the National Super League were also eliminated from the competition following a loss to professional side Caledonia AIA 5–4 on penalties after the match ended 2–2 in regulation.
In the remaining all-Pro League matches, North East Stars defeated Ma Pau 1–0 and Defence Force (PL) beat St. Ann's Rangers by a 3–1 scoreline.
San Juan Jabloteh secured the Trophy following an early goal from Kennedy Hinkson in the 2nd minute and superb goalkeeping from Cleon John to defeat the North East Stars 1–0.