I have no idea who the last five players were, but the very last one was Craig MacTavish, who is the current head coach of the Edmonton Oilers. His last season was with the St. Louis Blues in 1996/97. When he retired at the end of that season he was the last player to not wear a helmet.
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Craig MacTavish was the last NHL player to not wear a helmet. He played for the Boston Bruins from 1979-1983.