Born in Auburn, New York,[1] he began his career as a professional rider in 1978 and three years later went to compete at Woodbine Racetrack in Toronto.
In a career that spanned nineteen years, from 12,527 mounts he had 1,772 winners which earned purses totaling more than $39.5 million.
One of the top riders in the 1980s and very popular with the Woodbine fans,[3] Dave Penna rode primarily in Ontario at the Fort Erie Race Track in Fort Erie, and at Greenwood Raceway and Woodbine Racetrack, both in Toronto.
In 1995 at Monmouth Park in New Jersey he won his last Grade I race, the Philip H. Iselin Handicap.
[4] A racing accident resulted in an injury that forced Penna to retire in 1996 and for a short time he turned to training horses at Gulfstream Park.