The inaugural competition was contested between San Juan Jabloteh and W Connection, with the Savonetta Boys claiming their first title with a 1–0 win.

San Juan Jabloteh took the trophy in 2008 with a win over St. Ann's Rangers in Hasely Crawford Stadium.

In 2010, Ma Pau won their first competitive trophy after defeating North East Stars in the Classic's first final decided on a penalty shootout.

North East Stars defeated Defence Force 4–2 on penalties after the match ended in a 2–2 draw in the 2012 final.

[3] The knockout tournament begins in the first round with all TT Pro League teams automatically entering the competition.