It was owned by Toronto businessmen Abe Orpen, Charles Vance Millar, H. D. Brown and Thomas Hare.

In 1916, partners Charles Millar, H. D. "Curly" Brown, Abe Orpen and Thomas Hare built the Kenilworth Park Racetrack on 85 acres (34 ha) just outside Windsor, Ontario.

Orpen attempted to stop the new track by challenging its license and then threatening that anyone who raced at Devonshire would be banned from Kenilworth.

[6] In 1920, Orpen out-bid several racetracks to land a match race between Man o' War and Triple Crown winner Sir Barton at the track.

The Kenilworth Park Gold Cup was so highly anticipated that it became the first horserace to be filmed in its entirety, with the resulting footage later shown in movie theatres across the country.

The October 12, 1920, race was originally intended to be a face-off between the three great horses of the time: Man o' War, Sir Barton and Exterminator.

In his will, every duly ordained Christian minister in Walkerville, Sandwich and Windsor, "except Spracklin, who shot a hotelkeeper" was to receive a share of Kenilworth Park.

The track had lost CA$43,000 on an early spring meet run in May 1934, the dates selected to avoid competing with the Detroit races.