Cupolo was born in Niagara Falls, Ontario. He began his career at Memorial School and graduated to play minor hockey in the Falls.\n', '

In 1941, he was recruited by Stratford, where he won the Junior B title in 1941-42. The following season the team moved up to Major Junior "A" and became known as the Stratford Kroehlers.\n', '

The Boston Bruins invited him to their camp in 1943. Cupolo went to enlist in the armed forces, but was diagnosed with tuberculosis and faced a 14-month recovery.\n', '

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