As a champion bicycle racer, Cooper was a contemporary of Barney Oldfield, Carl G. Fisher, Johnny Johnson, Arthur Gardiner, "Plugger Bill" Martin and Eddie Bald.

At the 1898 League of American Wheelmen championship race on the Newby Oval in Indianapolis, Cooper won the half-mile professional event.

In the final day of practice for the 1905 American Elimination Trial, Cooper's Matheson had a faulty lubricating system, destroying the main engine bearing.

Bicycle racers, mechanics, race car drivers, they even owned a gold mine together in Colorado at the turn of the 20th century.

In January 1906, they attempted to parlay their renown as race drivers into an easier way to generate large sums of money.

Together they created a special effect using two race cars (the Peerless Green Dragon and the Peerless Blue Streak), bags of dirt, two large treadmills and stage props to create the illusion of a motor race for a Charles Dillingham play, The Vanderbilt Cup, starring Elsie Janis.

The show was a success but Oldfield and Cooper tired of the acting lifestyle in less than three months and returned to auto racing full-time.