| CHAMPION OWNERS AT CAYMANAS PARK | |||
| Year | Names | Races Won | Stakes ($) |
| 1959 | Mr. P.W. Chung | 8 | 9,930.00 |
| 1960 | Mr. P.W. Chung | 23 | 13,115.00 |
| 1961 | Mr. P.W. Chung | 23 | 16,285.00 |
| 1962 | Mr. P.W. Chung | 26 | 25,468.00 |
| 1963 | Mr. P.W. Chung | 15 | 10,710.00 |
| 1964 | Mr. P.W. Chung | 8 | 8,780.00 |
| 1965 | Mr. Ivan Lyn | 13 | 13,310.00 |
| 1966 | Mr. Tony MacKenzie | 19 | 14,950.00 |
| 1967 | Mr. Tony MacKenzie | 30 | 27,540.00 |
| 1968 | Mr. Tony MacKenzie | 16 | 27,970.00 |
| 1969 | Messrs. Lai & Rose | 13 | 18,140.00 |
| 1970 | The U.N.4 | 13 | 19,530.00 |
| 1971 | The U.N.4 | 18 | 31,840.00 |
| 1972 | Mr. E.A. Lai | 22 | 43,594.00 |
| 1973 | Mr. P. DuQuesnay | 32 | 67,125.00 |
| 1974 | Supreme Farms | 38 | 80,815.00 |
| 1975 | Melvin Park Stud & Stables | 24 | 71,757.00 |
| 1976 | Mr. Cecil C. Charlton | 33 | 112,391.00 |
| 1977 | Mr. Cecil C. Charlton | 43 | 129,050.00 |
| 1978 | S & G. Stables | 27 | 180,320.00 |
| 1979 | S & G. Stables | 24 | 152,785.00 |
| 1980 | S & G. Stables | 22 | 173,850.00 |
| 1981 | Turnbull Farms Ltd. | 20 | 172,915.00 |
| 1982 | Mr. Arthur Chin Fatt ET | 14 | 184,055.00 |
| 1983 | Arevlis & Associations | 10 | 301,405.00 |
| 1984 | Fast Lane | 14 | 350,985.00 |
| 1985 | Wonderland Syndicate | 23 | 470,440.00 |
| 1986 | Wonderland Syndicate | 21 | 280,405.00 |
| 1987 | P.T.A. | 10 | 356,025.00 |
| 1988 | Brah Syndicate | 327,020.00 | |
| 1989 | The Roman Syndicate | 10 | 566,100.00 |
| 1990 | The Roman Syndicate | 7 | 500,110.00 |
| 1991 | Mayer M Matalon O.J. & Hon. Patrick H.O. Rousseu O.J. | 3 | 969,490.00 |
| 1992 | Lakeland Farms Limited | 18 | 1,323,530.00 |
| 1993 | P. Feanny, Dr. C. Bradford & I. Clarke | 13 | 2,688,500.00 |
| 1994 | Frozen Four | 6 | 2,792,050.00 |
| 1995 | Richard N. Azan | 10 | 5,606,430.00 |
| 1996 | Lakeland Farms Limited | 21 | 5,511,000.00 |
| 1997 | Richard N. Azan | 17 | 6,612,050.00 |
| 1998 | Laurence E. Heffes | 22 | 6,471,800.00 |
| 1999 | Richard N. Azan | 34 | 11,379,280.00 |
| 2000 | Richard N. Azan | 17 | 7,629,450.00 |
| 2001 | Richard N. Azan | 36 | 11,838,580.00 |
| 2002 | Richard N. Azan | 23 | 10,480,355.00 |
| 2003 | Richard N. Azan | 22 | 9,340,500.00 |
| 2004 | Ruth A. Hussey | 38 | 11,675,250.00 |
| 2005 | Alexander Haber | 32 | 12,701,700.00 |
| 2006 | Hamark Farms | 29 | 12,314,600.00 |
| 2007 | Hamark Farms | 20 | 11,187,150.00 |
| 2008 | Elias Haloute | 24 | 17,630,500.00 |
| 2009 | Ruth A. Hussey | 24 | 14,957,750.00 |
| 2010 | Elite Bloodstock Ltd. | 17 | 22,455,800.00 |
| 2011 | Elite Bloodstock Ltd. | 17 | 16,554,150.00 |
| 2012 | Elite Bloodstock Ltd. | 18 | 14,272,450.00 |
| 2013 | Carlton Watson | 30 | 17,869,800.00 |
| 2014 | Elite Bloodstock Ltd. | 24 | 16,153,050.00 |
| 2015 | Elite Bloodstock Ltd. | 16 | 14,536,750.00 |
| 2016 | Stephan Aubyn B. Narinesingh | 21 | 21,695,000.00 |
| 2017 | Winston Allan Kong | 11 | 20,922,350.00 |
| 2018 | Stephan Aubyn B. Narinesingh | 33 | 23,166,125.00 |
| 2019 | Michros | 28 | 28,736,450.00 |
| 2020 | Michros | 22 | 25,306,900.00 |
| 2021 | Carlton Watson | 35 | 23,683,715.00 |
| 2022 | Carlton Watson | 34 | 25,898,590.00 |
| 2023 | Carlton Watson | 26 | 33,189,300.00 |
| 2024 | Carlton Watson | 30 | 53,512,900.00 |
| 2025 | Carlton Watson | 43 | 46,010,650.00 |









