| 1999 | Bryant Cumberbatch / Steven Brandon | Rhett Cumberbatch / Bryant Cumberbatch | Gavin Cumberbatch / Shawn Simpson | Gavin Cumberbatch / Shawn Simpson | Khamal Cumberbatch / Darien Benn |
| 1998 | Not held | Not held | Not held | Not held | Khamal Cumberbatch / Chemar Burnham |
| 1997 | Not held | Not held | Not held | Not held | Khamal Cumberbatch / Zachary Proverbs-Harris |
| 1996 | Rhett Cumberbatch / Bryant Cumberbatch | Gavin Cumberbatch / Shawn Simpson | Gavin Cumberbatch / Jonathon Johnson | Jonathon Johnson / Christian Duncan | (Mixed) 1st Benjamin Griffith / 2nd Shemane Griffith |
| 1995 | Gavin Cumberbatch / Shawn Simpson | Gavin Cumberbatch / Douglas Fitzgerald | Sam Taylor / Peter Barnard | Ryan Truss / Randy Clarke | Shemane Griffith / Benjamin Griffith |
| 1994 | Gavin Cumberbatch / Rhys Palmer | Sam Taylor / Gavin Cumberbatch | Sam Taylor / Tristan King | Dean Serrao / Ryan Truss | Stewart St. John / Shemane Griffith |
| 1993 | Gavin Cumberbatch / Daniel Bethell | Bryn Palmer / Sam Taylor | Ryan Truss / Sam Taylor | Ryan Truss / Randy Clarke | Stewart St. John / Zaki Williams |
| 1992 | Sam Taylor / Samuel Neilands | Bryn Palmer /Craig Allison | Ryan Truss / Vaughn Chalwell | Cleve Chalwell / Barry Everett | Matthew Mackenzie / Johann Haywood |
| 1991 | Bryn Palmer / Samuel Neilands | Ryan Truss / Daniel St. Victor | Richard Moorjani / Andre Ramsahoye | Richard Moorjani / Cleve Chalwell | Jonathan O’Dowd / Matthew Mackenzie |
| 1990 | Danny Atwell / Anthony Chalwell | Cleve Chalwell / Callum Samuel | Richard Moorjani / Amancio Guadagnino | Shane Johnson / Ryan Evelyn | Jonathan O’Dowd / Moishe Steinbok |
| 1989 | Ryan Truss / Daniel St. Victor | Richard Moorjani / Barry Everett | Richard Moorjani / Billy Tempro | Shane Johnson / Ryan Evelyn | Ciaran Raymer / Ryan Foster |
| 1988 | David Taylor / Daniel St. Victor | Richard Moorjani / Amancio Guadagnino | Chad Skelton / Martin Monplaisir | Tony Brackin / Shane Johnson | Ciaran Raymer / Jonathan O’Dowd |
| 1987 | David Taylor / Daniel St. Victor | Billy Tempro / Amancio Guadagnino | Shane Johnson / Michael Grant | Tony Brackin / David Bryan | Bryant Cumberbatch / Nkosi Ross |
| 1986 | Richard Moorjani / Timothy Richardson | Damian Edghill / Kolen Mackey | Michael Grant / Terry Rampersad | Tony Brackin / David Bryan | Alex Garcia / Nkosi Ross |
| 1985 | Ian Durant / Graeme Manning | Michael Grant / Shane Johnson | Shane Johnson / David Bryan | Glenn Johnson / David Bryan | Bryant Cumberbatch / Rhett Cumberbatch |
| 1984 | Damian Edghill / Ryan Webber | Shane Johnson / Damian Edghill | Gregory Austin / Glenn Johnson | Michael Fields / Gregory Austin | Rhett Cumberbatch / Bryant Cumberbatch |
| 1983 | Shane Johnson / Damian Edghill | Shane Johnson /Damian Edghill | Glenn Johnson / Slade Callaghan | Michael Fields / Michael Gomes | Rhett Cumberbatch / Bryant Cumberbatch |
| 1982 | Shane Johnson / Damian Edghill | Richard Chin / Mark Cyrus | Paul Cyrus / Mark Cyrus (Richard Chin) | Alan Ache / Michael Fields | Fabian Goodridge / Shawn Simpson |
| 1981 | Not held | Paul Cyrus / Richard Chin | Paul Cyrus / Michael Gomes | Mark Cox / Ian Hutchinson | |
| 1980 | Not held | Unknown / Unknown | Not held | Glenn Cheong /Wayne Burrowes | |
| 1979 | Not held | Wayne Burrowes / Derek Johnson | Not held | Mark Sealy / Mark Co | |
