the Triple Crown. In 1941, Triple Crown winner Whirlaway finished second in the Derby Trial, but returned to sweep the Derby, Preakness Stakes and Belmont Stakes. Records Speed record 1:28.45 - Macho Again (2008) (at distance of furlongs) 1:34.18 - Competitive Edge (2015) (at distance of one mile) Most wins by a jockey 4 - Eddie Arcaro (1948, 1949, 1952, 1959) 4 - Pat Day (1987, 1991, 1993, 2000) Most wins by a trainer 5 - Ben A. Jones (1943, 1947, 1948, 1951, 1952) Most wins by an owner 9 - Calumet Farm (1943, 1947, 1948, 1951, 1952, 1956, 1958, 2017, 2018) Winners See also Road to the Kentucky Derby References The 2009 Derby Trial Stakes at the NTRA Churchill Downs horse races Flat horse races for three-year-olds Triple Crown Prep Races Graded stakes races in the United States Recurring sporting events established in 1924 1924 establishments in Kentucky May events Grade 3 stakes races in the United States