Van Cleve became one of the earliest known people paid to play football when he, Ollie Rafferty, and Peter Wright signed contracts with the Allegheny Athletic Association for $50 per game for the entire 1893 season.

[9] During the 1895 season, Allegheny did not field a team after learning the club was under investigation by the Amateur Athletic Union for secretly paying its players.

[3][13] Prior to his professional career, Van Cleve played college football at Lehigh University, where he studied electrical engineering.

On October 15, 1892, Van Cleve scored Lehigh's only touchdown in a loss against the Orange Athletic Club.

[17] Van Cleve served as the head football coach at Pittsburgh Catholic College of the Holy Ghost—later renamed Duquesne University—in 1898.