At this point, a match race was organized between American Eclipse and James J. Harrison’s noted horse Sir Charles.

Sir Charles, with 20 wins to his credit, injured himself in a workout, and Harrison was required to forfeit the match, which American Eclipse won.

A second match was arranged only a single heat, and this time Sir Charles raced but broke down, leaving American Eclipse an easy winner.

By the time the race came round, two Southern horses had pulled out: Washington for proving not good enough in his training, and John Richards for injury.

So were the Vice-President of the United States, Daniel Tompkins, and the infamous Aaron Burr, who had shot and killed Alexander Hamilton in a duel about 19 years earlier (July 11, 1804).

The famed turf historian Cadwallader R. Colden (who wrote under the name "An Old Turfman”) said that American Eclipse was ridden badly by Crafts, who whipped and spurred him in the first heat.

William Crafts was replaced after this heat by the noted Samuel Purdy, who had retired but gladly rode a horse he'd ridden in his youth.

American Eclipse produced numerous stakes winners and others including Ariel, a filly who won 42 of 57 starts, including 18 four-mile heats; Black Maria (out of Lady Lightfoot, his old rival) who won 11 races with three- and four-mile heats; Lize (second dam of Enquirer); Ten Broeck (not the Nantura Farm Ten Broeck); Monmouth Eclipse; Bay Maria; and Gano.