The draw for the first round for the fifth edition of the tournament was conducted by Pro League CEO Dexter Skeene on 28 October 2009, at the TOYOTA Trinidad and Tobago Limited Barataria showroom.
St. Ann's Rangers, San Juan Jabloteh, Defence Force, and Joe Public were drawn as the top seeds in Groups A, B, C, and D, respectively.
On the competition's opening night, W Connection dumped Caledonia AIA out of the tournament with a 3–0 victory on penalty kicks after each team scored a goal in regulation.
Likewise, St. Ann's Rangers needed eight penalty kicks to defeat the lone National Super League team left in the tournament, 1976 FC Phoenix.
[3] Ma Pau and Joe Public continued their run to the semifinals with wins over Pro League sides W Connection and Defence Force respectively.