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Question:

Has anyone ever dropped the Stanley Cup while hoisting it on the ice?

In the victory ceremony right after the final game, has anyone ever dropped the Cup onto the ice, and if so, was it repaired?

Answer:

In 1905, a member of the Ottawa Senators tried to drop kick the Cup across the Rideau Canal. In 1962, the Toronto Maple Leafs won the Stanley Cup. During a party after the win, the trophy was dropped in a bonfire and badly damaged. It was repaired at the expense of the team. The trophy was dented the previous day, when a player dropped it during a locker room celebration, Bolt said.[35] That's what I could find. So the Bolts have dropped it in the locker room, the two other ones were way after the celebration on the ice.
This Site Might Help You. RE: Has anyone ever dropped the Stanley Cup while hoisting it on the ice? In the victory ceremony right after the final game, has anyone ever dropped the Cup onto the ice, and if so, was it repaired?
I don't know about the Stanley Cup, but I know the Windsor Spitfires of the OHL broke the Memorial Cup after winning.^.^

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