Herman Son Winningham (born December 1, 1961 in Orangeburg, South Carolina) is a former professional baseball player. He played all or part of nine seasons in Major League Baseball, primarily as a center fielder, for the New York Mets, Montreal Expos, Cincinnati Reds and Boston Red Sox.

Drafted by the New York Mets in the 1st round of the 1981 amateur draft, Winningham made his major league debut with the Mets on September 1, 1984. At one time a highly regarded prospect in the New York Mets chain, he was a part of the Gary Carter trade, along with Hubie Brooks, Floyd Youmans and Mike Fitzgerald. His talents never caught up to his statistics as he was primarily a reserve outfielder for most of his career. His final game was with the Boston Red Sox on October 3, 1992.

Winningham was a member of the Cincinnati Reds team that defeated the Pittsburgh Pirates in the 1990 National League Championship Series and the Oakland Athletics in the 1990 World Series. In the last game of the World Series he replaced an injured Billy Hatcher, went 2-3 and scored the winning run. During the 1990 postseason, he batted .364.