The Match Race

Man o' War's final race was the Kenilworth Park Gold Cup. Kenilworth Park is located in Canada, home of the champion, Sir Barton. Match races are not allowed in Canada, so they enlisted the mighty Exterminator to enter the race. Ultimately, however, Exterminator scratched from the Gold Cup and actually ran a race elsewhere that same day.

Sir Barton is considered to be the very first Triple Crown Winner, though the "Triple Crown" did not exist at the time. It wasn't until much later that the American Triple Crown of horse-racing became the race series that it is today. Some years, the Preakness was run before the Kentucky Derby, or they would be separated by only a few days. Nevertheless, Sir Barton did win the three races in order. As a 4-year-old, he was considered more mature, and, rather than Man o' War giving weight to his opponent, the elder horse carried more. Man o' War beat Sir Barton by a fair margin. After this, the owner and trainer decided to retire him. He had already easily won races carrying up to 138 pounds. It was felt that handicappers would pile too much weight on a 4-year-old Man o' War, and both owner and trainer decided it was best to retire Man o' War healthy and sound.