At age two, Not Bourbon set a new Woodbine track record in winning the Bull Page Stakes.
On June 22, 2008, Not Bourbon captured the $1 million Grade I Queen's Plate, edging out the hard-charging filly Ginger Brew.
[1] In the July 13th Prince of Wales Stakes, the second leg of the Canadian Triple Crown series, Not Bourbon finished sixth after flipping his palate during the race.
For his 2008 performances, Not Bourbon was voted the Sovereign Award for Champion 3-Year-Old Male Horse.
Charles E. Fipke, the colt's breeder, is also the owner of Tale of the Ekati, who finished 4th after a good trip in the 2008 Kentucky Derby.