Cunningham was a member of the powerful 1967 Sixers championship team (featuring Wilt Chamberlain, Hal Greer, Chet Walker, and Luke Jackson). After Chamberlain left the team in 1968, Cunningham became the 76ers' franchise player. He would replace the injured and aging Luke Jackson as the starting power forward of the team, and averaged 24.8 points per game and 12.8 rebounds per game during the 1968–69 season while leading the 76ers to 55 wins. After that season, he earned the first of what would be three straight All-NBA First Team selections.