Day learned to ride from his father, who owned a car repair shop in the ranching community of
Brush, Colorado. Day was the leading jockey by number of wins in 1982, 1983, 1984, 1986, 1990, 1991. Day rode winners of
American Triple Crown races nine times, ranking him behind
Eddie Arcaro's 17 wins in Triple Crown races as well as
Bill Shoemaker's 11, while tied with
Gary Stevens,
Bill Hartack and
Earl Sande's 9 each. However, Day had a comparatively poor Kentucky Derby record with only one win in twenty two tries. Some of Day's losses on top horses in the Kentucky Derby included
Easy Goer,
Forty Niner,
Summer Squall, Demon's Begone,
Corporate Report,
Tabasco Cat,
Timber Country,
Favorite Trick, Ten Most Wanted and
Menifee, who finished second behind
Charismatic in both the Kentucky Derby and the Preakness Stakes. He had been the regular rider of 1990 Derby winner Unbridled but chose to ride Summer Squall in that race instead. Pat Day's first and only Kentucky Derby victory was in 1992 aboard longshot
Lil E. Tee. On the day of that race, future
Belmont Stakes and
Breeders' Cup Classic winner
A.P. Indy was forced to scratch from the race due to a foot injury.
Arazi, the
American Champion Two-Year-Old Colt and
Breeders' Cup Juvenile winner, became the heavy favorite. Day rated behind Arazi in tenth place, hoping to follow his move and take second place. But when asked for run, Lil E. Tee responded by sweeping past Arazi for the win. "To say the least, it was very satisfying," said Day. In 1991, Pat Day won the
Canadian Triple Crown and the
Breeders' Cup Distaff aboard the future Hall of Fame filly
Dance Smartly. He is the only jockey to have ridden at least one mount in each of the first 20
Breeders' Cups, and at one point was the all-time leader in Breeders' Cup winners, with 12. Day made his base in Kentucky, where he rode at Churchill Downs and Keeneland in the spring and fall. In the winter, he originally rode at
Oaklawn Park in Arkansas, switching in the mid-1990s to
Gulfstream Park. In the summer, he originally rode at
Arlington Park, later switching to
Saratoga. With the change in circuits, Day's number of wins decreased but his earnings increased. Day won his first earnings title in 1999, followed by another win in 2000 in a close battle with Jerry Bailey. Day finished 2000 with his mounts earning $17,479,838 in purses (recording 267 wins from 1,219 starts). Bailey finished with $17,468,690 in earnings.
Triple Crown top three finishes Day recorded nine wins in the
American Triple Crown plus ten second-place finishes and four thirds. ;Kentucky Derby • 1988 on
Forty Niner (2nd) • 1989 on
Easy Goer (2nd) • 1990 on
Summer Squall (2nd) • 1992 on
Lil E. Tee (1st) • 1995 on
Timber Country (3rd) • 1996 on Prince of Thieves (3rd) • 1999 on
Menifee (2nd) ;Preakness Stakes • 1985 on '''
Tank's Prospect''' (1st) • 1989 on
Easy Goer (2nd) • 1990 on
Summer Squall (1st) • 1991 on Corporate Report (2nd) • 1993 on
Cherokee Run (2nd) • 1994 on
Tabasco Cat (1st) • 1995 on
Timber Country (1st) • 1996 on
Louis Quatorze (1st) • 1999 on
Menifee (2nd) ;Belmont Stakes • 1984 on Pine Circle (2nd) • 1987 on
Gulch (3rd) • 1989 on
Easy Goer (1st) • 1994 on
Tabasco Cat (1st) • 2000 on
Commendable (1st) • 2003 on Ten Most Wanted (2nd) • 2004 on Royal Assault (3rd)
Breeders' Cup wins Day won twelve Breeders' Cup races. ;
Breeders' Cup Classic • 1984 on
Wild Again • 1990 on
Unbridled • 1998 on
Awesome Again • 1999 on
Cat Thief ;
Breeders' Cup Distaff • 1986 on
Lady's Secret • 1991 on
Dance Smartly • 2001 on Unbridled Elaine ;
Breeders' Cup Turf • 1987 on
Theatrical ;
Breeders' Cup Juvenile • 1994 on
Timber Country • 1997 on
Favorite Trick ;
Breeders' Cup Juvenile Fillies • 1987 on
Epitome • 1994 on
Flanders ==Records==