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
รngel 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 Vรกsquez 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