However, only three clubs from 4 of the 6 regional football associations were awarded qualification into this year's edition, with the Eastern Counties and Northern FA as the exceptions as they only received two.
1976 FC Phoenix and WASA provided the Trophy's first two upsets over Pro League clubs by putting out Joe Public and North East Stars, respectively.
[3] Another surprise from the round was that Dathea Copious Suns defeated T&TEC to be the lone representative from the third level of the pyramid in the quarterfinals.
WASA remained the only club from outside the TT Pro League to advance to the semifinals after defeating Dathea Copious Suns.
[4] Caledonia AIA needed extra time to defeat St. Ann's Rangers (PL),[5] Defence Force stunned San Juan Jabloteh 2–1,[6] and W Connection put out giant-killers 1976 FC Phoenix to advance to the semifinals.
W Connection made quick work of Super League side WASA to end their run in the competition by putting up eight goals.