Trained by Richard Dutrow Jr., Digger raced five times as a two-year-old, all at Laurel Park. Broke his maiden after three consecutive second-place finishes, and then finished third in his final race of the year, the $75,000 Maryland Juvenile Championship.
Started his three-year-old season with a win in an allowance race at Laurel Park. Finished ninth in the $100,000 John Battaglia Memorial Stakes at Turfway Park, and then finished second in an allowance race at Charlestown.
Digger was entered in the $60,000 Spend a Buck Stakes at Monmouth Park but was scratched out of that race and entered in the Belmont Stakes after Street Sense was pulled out.