Win Headley (born July 4, 1949) is a former American football offensive guard who played one season with the Montreal Alouettes of the Canadian Football League (CFL).
He was drafted by the Green Bay Packers of the National Football League (NFL) in the eighth round of the 1971 NFL Draft.
He played college football at Wake Forest University and attended Staples High School in Westport, Connecticut.
Headley was also a member of the Hartford Knights of the Atlantic Coast Football League (ACFL).