Winter was chosen to start on Opening Day of the 1903 Boston season, defeating Rube Waddell and the Philadelphia Athletics, 9–4, at Huntington Avenue Grounds. He also wound up pitching in the game in which the Americans clinched the pennant, although he did not play in the 1903 World Series as Boston used only Cy Young, Bill Dinneen and Long Tom Hughes. Winter worked as a ticket taker during the series. He was intermittently effective during the 1903 season, which the 1904 "Reach Guide" attributed to not being fully recovered from his illness.