San Juan Jabloteh entered as the tournament's defending champion, who defeated North East Stars 1–0 in the 2010–11 final at Marvin Lee Stadium.
[3] As a result of the random draw, two TT Pro League clubs were drawn into the first round of the competition with Caledonia AIA facing Uprising Youths and Defence Force squaring off with St. Anthony's College.
However, both clubs progressed into the second round with the Morvant/Laventille Stallions recording a 4–1 victory and the Teteron Boys narrowly defeating the Secondary Schools Football League team 3–2.
[12][13] Following the draw, three matches featured all-Pro League encounters with Defence Force advancing with a narrow 3–2 win over Police, Caledonia AIA upending North East Stars 4–3 on penalties after the match ended 1–1 in regulation, and W Connection eliminating the defending champions San Juan Jabloteh 1–0 with a goal from Shahdon Winchester.
[18] Caledonia AIA used goals from Devorn Jorsling and Ataullah Guerra to defeat Joe Public 2–0 and advance to the semifinal round.
[19] In addition, W Connection ended the cinderella run of Scarborough Secondary following a dominant 5–0 win with Hashim Arcia recording a hat-trick.
In the only match involving teams outside the top flight, WASA from the National Super League defeated OJ's Soldado All-Stars 3–1.
On 18 March 2012 at the Manny Ramjohn Stadium, W Connection lost to Caledonia AIA 1–0 with a goal from Ataullah Guerra in the 35th minute to propel the Morvant/Laventille Stallions into the final.
[23][24] The leading goal scorer of the tournament was jointly held by Michael Edwards of Defence Force and Andrew London of Club Sando.