A speedy outfielder who struggled at the plate in the majors, Winningham was one of four players traded from the New York Mets to the Montreal Expos for Gary Carter in December 1984. He started in centerfield for the Expos in 1985 until his June knee injury gave Mitch Webster a chance to play.
Winningham stole a career-high 29 bases in 131 games for Montreal in 1987, then was traded to the Cincinnati Reds in 1988, where he remained a reserve. Aside from a .407 average in fourteen games with the Mets in 1984, Winningham hit better than .237 only once in the big leagues. He ended his major-league career batting .235 for the Boston Red Sox in 1992