In his 10-year major league career, he played mostly for the Cleveland Spiders, compiling a win–loss record of 163–98.

[5] Cuppy then joined the National League's Cleveland Spiders, and for the next few seasons, he was the team's number two starter behind Cy Young.

[11] Cuppy remained with the Spiders until March 29, 1899, when the club's owners transferred him, along with the majority of the roster, to their other team, the St. Louis Perfectos.

[3] Cuppy finished his major league career with a record of 163–98 and a 3.48 ERA in 2,283 innings pitched.

[8] He was known for taking his time between pitches while on the mound, which annoyed fans, umpires, opposing batters, and his own teammates.

[1][4][12] Cuppy died at the age of 53, of Bright's disease, on his farm in Elkhart, Indiana.