A first-team All-American his senior year, he led the 1928–29 team to a 17–3 record and was the second-leading scorer in the nation.

[2] His lone major league appearance came on September 15, 1929, in the Senators' 16–2 loss to the Detroit Tigers at Griffith Stadium.

He took the mound in the sixth inning with the Tigers already holding a 12–2 lead, entering the game as part of a double switch in which he took the place of Baseball Hall of Fame shortstop Joe Cronin in the Washington lineup.

Wineapple hurled the final four innings in relief, giving up four runs (two earned) on seven hits, walking three and striking out one against a Tigers lineup that featured Hall of Famer Charlie Gehringer.

[7][8] Wineapple was inducted into the Providence College sports hall of fame as part if its inaugural class of 1970.