While the series was not officially called the Triple Crown yet, Sir Barton (below) was the first horse to win the Kentucky Derby, Preakness, and Belmont Stakes in the same year, 1919. The following year, Man o' War did not compete in the Derby but shattered records in both the Preakness and Belmont, raising the question of who was truly the better horse. Even though they were a year apart in age, and Sir Barton reportedly was dealing with minor injuries, they faced off with great hype in the Kenilworth Park Gold Cup. Man o' War triumphed easily.