[3] In 1921, former jockey turned trainer Willie Knapp put Kelsay on the future Hall of Fame gelding Exterminator to win the Autumn Stakes at the Old Woodbine Race Course in Toronto, Canada.
[4] Competing at Havana's Oriental Park Racetrack in 1922, Willie Kelsay had wins in two premier events that regularly drew some of the top American stables.
On February 12 he rode the Goldapple Stables' colt Billy Barton to victory in the Cuban Grand National Handicap for trainer Frank Bray.
[8] Among Kelsay's other significant wins, in 1928 and 1929 he rode the winner of the Empire City Derby[9] and in 1930 won the Carter, Fleetwing and Manhattan Handicaps, plus the Hopeful Stakes, all of which were for Gifford Cochran's stable under future Hall of Fame trainer, Henry McDaniel.
[10][11][12] The following year, Kelsay was part of another success story with a two-year-old horse when he rode the undefeated Vander Pool to win the 1930 editions of the Youthful, Bowie Kindergarten and Aberdeen Stakes, the latter a race he had earlier won with Careful.