Day a four-time Eclipse Award winner also received the George Woolf Memorial Jockey Award in 1985, given annually to a North American jockey who demonstrates the highest standards of professional and personal conduct.

Day has ridden winners of U.S. Triple Crown races nine times that include: Kentucky Derby - 1992; Preakness - 1985, 1990, 1994-96

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 ranks second all-time in Breeders' Cup winners, with 12:

Breeders' Cup Classic - 1984, 1990, 1998, 1999
Breeders' Cup Distaff - 1986, 1991, 2001
Breeders' Cup Juvenile - 1994, 1997
Breeders' Cup Juvenile Fillies - 1987, 1994
Breeders' Cup Turf - 1987

In 1989, he set a North American record when he won eight of nine mounts in a single day at Arlington Park.

After undergoing hip surgery that forced him to miss the Derby for the first time in 21 years, Day announced his retirement on August 3, 2005 after a 32-year career that saw him ride 8,804 winners, fourth on the all-time list, and set a North American record for prize money won, with his mounts earning nearly USD 298 million.