Dexter's career in baseball started in 1889, with the Evansville Cooks, a semiprofessional ball club. He played with them until 1894 when he decided to attend University of the South. He also played for the Louisville Colonels, Boston Braves, and Chicago Cubs organizations.
On December 30, 1903 Charlie Dexter and fellow player John Franklin Houseman were in a box watching a show at the Iroquois Theatre in Chicago when the Iroquois Theatre fire broke out; they were credited with breaking down a locked door and rescuing a number of people.
In 1905, he reportedly stabbed Milwaukee Brewers first baseman Quait Bateman in the chest while he was drunk. Dexter was taken to jail. Bateman decided to not press charges as he believed it was an accident and Dexter was released the next morning.

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