The Canadian Horse Racing Hall of Fame Honours Man o’ War on the 100th Anniversary of historic race in Windsor, Ontario

October 12, 2020, marks the 100th anniversary of Man o’ War and Sir Barton match race at Windsor’s Kenilworth Park.  In honour of this historic Canadian horse racing event, the Canadian Horse Racing Hall of Fame is conducting a campaign via its social media channels honouring the great Man o’ War.  Beginning October 5th, the campaign will culminate in an online video celebration and a special announcement on October 12 at 2:00 pm to coincide with the 100th Anniversary of the race.

We invite you to join the celebration and announcement by following the Canadian Horse Racing Hall of Fame on Facebook, Twitter @Cdn_HallofFame or via the CHRHF’s website at

What some have called ‘the greatest day in Canadian horse racing’, the race took place in Windsor, ON in 1920 when the two biggest names of the day competed in a match race.

The immortal Man o’ War, holder of more records than any other horse and the leading three-year-old of 1920 was owned by Sam Riddle of Philadelphia, and Sir Barton, the Canadian-owned champion of the older-horse division and America’s first Triple Crown winner in 1919, owned by Commander J. K. L. Ross of Montreal faced off to settle the supremacy of the American turf.

Man o’ War, the original “Big Red” was the prohibitive 1-to-20 favourite, with bettors wagering a reported $220,000 on the race organized by the track’s operator Mr. Abe Orpen and considered a major coup in a time Canadian racing needed a boost following the government’s wartime ban on betting in 1918 and 1919.  It was a highly anticipated event that would become the first horse race filmed from wire to wire, with the footage later shown in movie theatres across the continent.

Known as the Kenilworth Cup, and originally proposed as a race that might also feature a third great horse of the time, Exterminator, but terms of the race at a mile and a quarter and a weight-for-age format were not to the liking of Exterminator’s owners so he was not entered, resulting in a match race between Man o’ War and Sir Barton.  The two competed for a $75,000 US purse and accompanying Gold Cup, designed by Tiffany & Co and valued at $5,000.  That same trophy later was later donated to Saratoga by Mrs. Riddle the wife of Man o’ War’s owner, is now known as the Man o’ War Cup and presented each year to the winner of The Travers Stakes.

In front of an estimated thirty thousand spectators, Sir Barton had the advantage at the start and led to the first pole by little more than a length.  At the half-mile Man o’ War had overtaken and passed the Ross horse to lead by two lengths.  By the three-quarters, the lead had been cut to a length and a half.  Man o’ War’s jockey responded by letting his mount out to open his lead to four lengths as they entered the stretch.  With Sir Barton being urged to his limit, Man o’ War continued to run effortlessly to cross the wire ahead by seven lengths, buoyed by cheers of the massive crowd, to lower the track record for a mile and a quarter by six and two-fifths seconds.

Following the race the Canadian Sportsman and Live Stock Journal carried a photo of Man o’ War on the cover of its October 18th issue accompanied by a caption reading “MAN O’ WAR – Winner of the $75,000 race at Windsor on Tuesday, October 12th, defeating Sir Barton in a most decisive manner and showing himself to be a wonder horse”.

Man o’ War’s lone race on Canadian soil was also his final career start and win before starting his breeding career, something that was repeated by “Old Bones” Exterminator and a later “Big Red”, Secretariat who also concluded their careers with wins at Canadian tracks.