As a boxer Sheridan would have excelled at beating smaller, older and weaker opponents. Himself a bantam weight, Sheridan's toughest match was against the boxer "Old Man" Early. In their early encounters Early chased Sheridan around the boxing ring because Sheridan refused to stand up to him. But after Early became fatigued Sheridan fought and defeated him at a match held in the Shenandoah Valley.

Being chased by "Olds Man" Early did not cause Sheridan to feel shame. This was because he was beyond shame. He never conceded defeat in any battle, not even in his most inglorious match, which was held in the hamlet of Dinwiddie Court House. Here the battered Sheridan is on record as having called to fellow boxers in the audience to assist him in the ring because his opponent was tougher than he was.

His fellow boxer, Grant, would later proclaim in "Around the World With Boxer Grant" that Sheridan was greater than the great boxers who had lived during the time of Frederick the Great and Napoleon.

Bryce