They first played in the Antigonish-Pictou-Colchester Senior Hockey League in 1929-30. After that senior hockey in Sydney was usually sponsored by local businesses and organizations. Starting in 1937-38 the Millionaires reapppeared. They dominated the Cape Breton Senior Hockey League for the next four seasons, winning three league titles in a row. In 1940-41 they made their one and only Allan Cup appearance, losing a tough final to the Regina Rangers. From 1942-43 to 1944-45 military teams took over the Cape Breton league.