Since 1875, the finest three-year-old in the United States have made tracks to run for the roses in the Kentucky Derby.
Over this near sesquicentenary, millions have poured through the gates at Churchill Downs, sipping mint juleps as these thoroughbreds tear up the one-a-quarter-mile track in what has become the most exciting two minutes in world racing.
Given the age-restriction, no horse has ever won the race on multiple occasions. However, the same cannot be said for the country's best jockeys, with the cream of the crop having saluted on several occasions.
Ahead of the 150th running this May, here are the 27 hoops to passed the Churchill Downs post first on multiple occasions.
| Jockey | Wins | Mounts | Winning percentage | Years won |
| Eddie Arcaro | 5 | 21 | 23.80% | 1938, 1941, 1945, 1958 & 1952 |
| Bill Hartack | 5 | 12 | 41.66% | 1957, 1960, 1962, 1964 & 1969 |
| Bill Shoemaker | 4 | 26 | 15.38% | 1955, 1959, 1965 & 1986 |
| Isaac Murphy | 3 | 11 | 27.27% | 1884, 1890 & 1891 |
| Earl Sande | 3 | 8 | 37.50% | 1923, 1925 & 1930 |
| Ángel Cordero Jr. | 3 | 17 | 17.64% | 1974, 1976 & 1985 |
| Gary Stevens | 3 | 22 | 13.63% | 1988, 1995 & 1997 |
| Kent Desormeaux | 3 | 22 | 13.63% | 1998, 2000 & 2008 |
| Calvin Borel | 3 | 12 | 25% | 2007,2009 & 2010 |
| Victor Espinoza | 3 | 10 | 30% | 2002, 2014 & 2015 |
| John Velazquez | 3 | 24 | 12.50% | 2011, 2017 & 2020 |
| Willie Simmins | 2 | 2 | 100% | 1896 & 1898 |
| Jimmy Winkfield | 2 | 4 | 50% | 1901 & 1902 |
| Johnny Loftus | 2 | 6 | 33.33% | 1916 & 1919 |
| Albert Johnson | 2 | 7 | 28.57% | 1922 & 1926 |
| Linus McAtee | 2 | 7 | 28.57% | 1927 & 1929 |
| Charley Kurtsinger | 2 | 4 | 50% | 1931 & 1937 |
| Conn McCreary | 2 | 10 | 20% | 1944 & 1951 |
| Ismael Valenzuela | 2 | 8 | 25% | 1958 & 1968 |
| Ron Turcotte | 2 | 5 | 40% | 1972 & 1973 |
| Jacinto Vásquez | 2 | 8 | 25% | 1975 & 1980 |
| Eddie Belahoussaye | 2 | 13 | 15.38% | 1982 & 1983 |
| Chris McCarron | 2 | 18 | 11.11% | 1987 & 1994 |
| Chris Antley | 2 | 17 | 11.76% | 1991 & 1999 |
| Jerry Bailey | 2 | 8 | 25% | 1993 & 1996 |
| Mike Smith | 2 | 28 | 7.14% | 2005 & 2018 |
| Mario Gutierrez | 2 | 3 | 66.66% | 2012 & 2016 |
