On November 4, 2006, Street Sense won the most important race for two-year-old colts in the United States, the Breeders' Cup Juvenile, by a record 10 lengths.

On March 17, in his first race as a three-year-old, he won the Tampa Bay Derby by half a nose over Any Given Saturday in a track record-breaking time for the one-and-one-sixteenth-mile distance.

Street Sense went into the second jewel of the Triple Crown as the favorite, but finished second by a nose to eventual two-time Horse of the year Curlin in the Preakness Stakes at Pimlico Race Course on May 19, 2007.

The 9-horse field included Derby runner-up Hard Spun, Curlin, sixth-place finisher Circular Quay, Mint Slewlep, Xchanger, King of the Roxy, Flying First Class, and C P West.

Street Sense closed out his career with a fourth-place finish on a sloppy track in the October 27, 2007, running of the Breeders' Cup Classic at Monmouth Park Racetrack.

After covering a few high quality books of mares and siring a slew of stakes winners in 2021 & 2022, Street Sense's fee gradually rose back to $75,000 (2020, 2022, 2023).