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Brandon's Cowboy won an elimination of the $1 million Metro Stake and was third to I Am A Fool in the $540,000 Breeders Crown at two. The following season he captured the $260,000 Berrys Creek, the $76,000 Robert Suslow, Reynolds Memorial, an elimination of the $640,000 Confederation Cup and was race-timed in 1:49.3.
In 2005 Brandon's Cowboy was an open class winner at Yonkers, took a 1:50.2 record at Woodbine and was race-timed in 1:48.4.
