2008 Trinidad and Tobago Pro Bowl

[1] The tournament commenced on 6 May, with 10 teams competing in single elimination matches and concluded on 23 May, with Caledonia AIA defeating Defence Force 2–0 to claim the title.

The automatic quarterfinal qualifiers in order of league position were: Caledonia AIA, W Connection, San Juan Jabloteh, United Petrotrin, Joe Public, and Defence Force.

In the qualifying round, St. Ann's Rangers defeated Tobago United 3–1, whereas North East Stars upended Ma Pau 1–0 to advance to the quarterfinals.

United Petrotrin advanced to the semifinals after they beat Joe Public with the lone goal from Beville Joseph.

[2] Using a double in W Connection's win over North East Stars, Oscar Velasco-Torijano was the tournament's leading goal scorer.