Ed Bolden founded the team in 1910 as an amateur athletic club for local young men. They won the first three Eastern Colored League pennants beginning in 1923 and in 1925 won the second Colored World Series. Hall of Fame player Judy Johnson was a Hilldale regular for most its professional era with 12 seasons in 15 years (1918–1932). Pitcher Phil Cockrell played for Hilldale throughout those years. Oscar Charleston, Biz Mackey, Louis Santop, Chaney White, and Jesse "Nip" Winters were also important Hilldale players in the 1920s.
Frustrated by the league's lack of organization, Bolden withdrew his club from the ECL prior to the 1928 season. When the American Negro League was organized in 1929, Hilldale joined, but the league lasted only one season. Bolden was subsequently forced out of club management, and Hilldale corporation member Lloyd Thompson assumed control of the club in 1930.