Out of Northern Dancer's granddaughter Cloudy Spot, he was sired by the 1980 American Champion Two-Year-Old Colt, Lord Avie.

In 2007, under trainer Frank Kirby, ridden by Ramsey Zimmerman, Cloudy's Knight won the richest and most important race of his career, the $2 million Grade 1 Canadian International Stakes at Woodbine Racetrack in Toronto, Canada.

[1] This win combined with his victory in Woodbine's G2 Sky Classic Stakes, contributed to his being voted Canada's Sovereign Award for Champion Male Turf Horse.

In 2009, following a year-long layoff as a result of a serious tendon injury, the nine-year-old gelding came back to another highly successful campaign for trainer Jonathan Sheppard.

Under Champion jockey Rosemary Homeister, Jr., Cloudy's Knight raised his career earnings to more than $2.4 million with wins in the Kentucky Cup Turf Stakes [2] and Sycamore Stakes [3] at tracks in Kentucky, a second by a nose in the mile and three-quarter Breeders' Cup Marathon at Santa Anita Park [4], and on December 6, he won in the mile and three-quarter Valedictory Stakes at Woodbine.