Chapman, who picked up basketball as a young boy, started playing as a guard for the Victoria Blue Ribbons with his younger brother Art. They won the Canadian title in their first season, and repeated in 1935. Restyled the Victoria Dominoes after their sponsor folded, Chapman was sad to lose to the Windsor Fords in 1936, as the champion team was also selected for the Berlin Olympics. However, Windsor was very impressed with their opponents, and invited several Victoria players, including Chuck and Art, to join them in Berlin. There, Canada only lost to the U.S. and came home with a silver medal. A top long-range shooter, Chapman captained the Dominoes to three more Canadian titles (1939, 1942 and 1946).