Many thanks to David Williams for this information. I only have the results up to 2001. I'm not sure if the tournament happened after that.
Year Winner Runners-Up Best Speakers
2001 UWI, Mona; Uni. Guayan; David Williams (UWI, Mona)
2000 UWI, Cave Hill; UWI, Mona; Stewart Rodney (UWI, Mona)
1999 UWI, Mona; UWI, Cave Hill; Danielle Archer (UWI, Mona)
1997 UWI, Mona
1996 Medgar Evers College
1995 UVI St. Thomas
1994 Uni. Guyana
1993 UWI, Cave Hill
1991 UWI, St. Augustine
1990 Uni. Guyana
1989 UWI, Mona
The first Caribbean Inter-Collegiate Debating Tournament was organized and held on the St. Thomas campus of the University of the Virgin Islands (UVI) in April 1989. It was the brain child of Ms. Junie M. Violenes, Student Activities Supervisor at UVI St. Thomas. She worked with an organizing team comprising Prof. Vaneer Godwin, Mr. Ronald Taplin (then Acting Director of Student Affairs), and student reps. Daley Phillips and Valencia Williams.
Since then, the debates have expanded to include the wider Caribbean, with other University campuses serving as host - University of the West Indies (UWI) St. Augustine in Trinidad and Tobago; Caribbean Research Center of Medgar Evers College (City University of New York); College of the Bahamas; Inter-American University, Puerto Rico; UVI, St. Croix; and UWI, Cave Hill in Barbados.