Charles Haley won 5 Super Bowl champion XXIII, XXIV, XXVII, XXVIII, XXX. Haley won two Super Bowls with the San Francisco 49ers in Super Bowl XXIII, XXIV and three with Dallas Cowboys in Super Bowl XXVII, XXVIII, XXX. San Francisco 49ers Won Cincinnati Bengals and Denver Broncos in Super Bowl XXIII and Super Bowl XXIV, Dallas Cowboys Defeated Buffalo Bills in 1992,1993. Dallas Cowboys won Pittsburgh Steelers in 1995. He was elected to the Pro Football Hall of Fame in 2015.