Thoroughbred racing made its debut at Caymanas Park in 1959, marking the beginning of a storied tradition. That same year, Blush claimed victory in the inaugural Jamaica Derby, trained by Gerry Skelton, ridden by Arthur Jones, and owned by Andrew H B Aguilar.
Since then, 65 editions of the Derby have been run at Caymanas Park, producing a rich history of competition and triumph. Among the standout owners:
Elias Haloute, a Barbadian racing enthusiast, leads the pack with four Derby wins, making him the most successful owner in the event’s history at Caymanas Park.
The owning syndicate of James Hardie and Dr.Victor Magnus follows closely with three victories.
Chevan Maharaj of Trinidad and Tobago, also boasts three wins, sharing second place in the rankings.
Following the 2025 Derby win by I Dream Again, Derrick Smith has joined the elite group of multiple-time winners, now with two Derby titles to his name.
Below is the list of the top Derby owners since racing started at Caymanas Park in 1959.
| OWNERS | YEAR | HORSES | TRAINERS | JOCKEYS |
| Elias Haloute | 1998 | Terremoto | Anthony Nunes | Charles Hussey |
| Elias Haloute & Stephan Narinesingh | 2011 | Techomoto | Anthony Nunes | Dick Cardenas |
| 2014 | Relampago | Anthony Nunes | Shane Ellis | |
| 2016 | Orpheus | Anthony Nunes | Shane Ellis | |
| James Hardie & Dr Victor Magnus | 1964 | Duesbury | Aston Cammock | Winston Ellis |
| 1969` | Buckchaser | Alan Williams | Kenneth Mattis | |
| 1971 | Reprieve | Aston Cammock | Richard Depass | |
| Chevan Maharaj | 2019 | Supreme Soul | Anthony Nunes | Shane Ellis |
| 2021 | Calculus | Gary Subratie | Shane Ellis | |
| 2024 | Crown Chaser | Anthony Nunes | Shane Ellis | |
| The Frozen Four | 1992 | Milligram | Philip Feanny | Winston Griffiths |
| 1994 | Wells Fargo | Philip Feanny | Charles Hussey | |
| Hamark Farms | 2003 | A King Is Born | Philip Feanny | Winston Griffiths |
| 2004 | Distinctly Irish | Philip Feanny | Winston Griffiths | |
| Derrick Smith | 2015 | Seeking My Dream | Wayne DaCosta | Omar Walker |
| 2025 | I Dream Again | Jason DaCosta | Robert Halledeen | |
| Patrick Lynch & Kevin McDonald | 2018 | Drone Strike | Patrick Lynch | Aaron Chatrie |
| Patrick Lynch | 2023 | Ability | Patrick Lynch | Allen Maragh |
