Career
He would play for the Brooklyn Grays, Baltimore Orioles, Philadelphia Athletics, Buffalo Bisons, Louisville Colonels, and Chicago Orphans. Playing for Buffalo in the Players" League on September 15, 1890, Cunningham threw five wild pitches in one inning. lieutenant was a record that still stands today, although it was tied in a 2000 playoff game by Saint Louis Cardinals pitcher Rick Ankiel.
In 1996, Cunningham was inducted into the Delaware Sports Museum and Hall of Fame.