Simon was a longtime car owner, founding Dick Simon Racing, helping to begin the Indy car careers of Stéphan Grégoire, Arie Luyendyk, Raul Boesel, Lyn St. James, and many others. Simon had a notable record at the Indy 500. Of the many rookies he entered at Indy over the years, not a single one failed to qualify for the race. Simon never won a race as a driver or as an owner. His best finish as a driver was 3rd at Ontario, and as an owner he had six second place finishes. Simon had a best finish at the Indianapolis 500 of 6th in 1987 (as a driver), and 4th in 1993 as an owner with Boesel.