Bred by Rod and Lorraine Rodriguez,[1] Old Fashioned was purchased for $800,000 by Rick Porter's Fox Hill Farms at the September 2007 Keeneland yearling sale and sent into training with Larry Jones.
Ridden by jockey Terry Thompson in his first two starts, he won his debut by a nose in a six-furlong event at Delaware Park Racetrack.
Old Fashioned was not entered in the 2008 Breeders' Cup Juvenile but ran instead in the November 29 Remsen Stakes at New York City's Aqueduct Racetrack.
Ridden by Ramon Dominguez, Old Fashioned won the 1+1⁄8 miles (1.8 km) Grade II event by 7+1⁄4 lengths while finishing under a hard hold.
In a December 26, 2008 article on the ESPN website, award-winning horse racing writer Bill Finley picked Old Fashioned as the number one contender for the first leg of the 2009 U.S.