He was inducted into the Horse Racing Hall of Fame in 2012, rode his 5,000th winner in 2013, and became the leading money-earning jockey in the history of the sport in 2014.

A winner of fifteen Breeders' Cup and six Triple Crown races including 2011, 2017, and 2020 Kentucky Derbies, Velázquez has also won major graded stakes races such as the Kentucky Oaks, Metropolitan Handicap, Whitney Handicap, Dubai World Cup, and Woodbine Mile.

Velazquez was born in Carolina, Puerto Rico and learned to ride there, attending a jockey school for a year and a half.

On January 3, 1990, he won his first race, aboard Rodas at El Nuevo Comandante racetrack in Canóvanas, Puerto Rico.

That same year, he moved to New York State and obtained guidance from leading jockey Angel Cordero Jr. Richie Allen was his first agent,[3] followed in 1992 by Ralph Theroux.

[4] Soon after moving to the United States in 1990, Velazquez won his first stakes race, the Ticonderoga at Aqueduct Racetrack.

In 1996, he won his first riding title at Aqueduct and also rode his first Eclipse Award winner, Yank's Music, trained by his father-in-law, to Championship Three-Year-Old Filly honors.

Rags to Riches stumbled at the start, then was taken wide by another horse around the first turn before Velazquez guided her to better position.

[17] That year, he rode Quality Road to a win at the Florida Derby, knocking off the previously unbeaten Dunkirk.

He was supposed to ride Uncle Mo, but his horse was scratched from the race due to stomach problems.

Then, due to an injury to Robby Albarado, Animal Kingdom's regular rider, Velazquez got the mount and won the race.

"[20] In the 2012 Belmont Stakes, Velazquez won his third Triple Crown Race aboard Union Rags.

On October 13, he became the all-time leading money winner among North American jockeys, surpassing Pat Day in the ninth race at Belmont aboard the filly Bit Bustin.

[7][23] His year ended abruptly during the Breeders' Cup weekend at Santa Anita on November 2 when his mount in the Juvenile Fillies fractured her leg and fell, throwing Velazquez, who was struck by one of the trailing horses.

This brought his lifetime total to fifteen, tying him for the second-most wins in Breeders' Cup history with Jerry Bailey, behind only Mike Smith.

[27] On November 30, 2018, Velazquez earned win number 6000 aboard Singapore Trader, trained by Todd Pletcher.

On May 1, 2021, he rode Medina Spirit, trained by two-time Triple Crown winner Bob Baffert, to victory in the 147th Kentucky Derby at Churchill Downs.