Kypreos was born in Toronto, Ontario. As a youth, he played in the 1979 Quebec International Pee-Wee Hockey Tournament with a minor ice hockey team from Wexford, Toronto. He was an effective goal scorer in juniors with the North Bay Centennials of the Ontario Hockey League (OHL). He finished second in the league for goals scored, with 62, in the 1985–86 OHL season, leading the top scoring Centennials to second place in the regular season.[citation needed]\n', '

Kypreos struggled to score at the NHL level and immediately became known as an enforcer, a role he maintained throughout his pro career. He was never drafted by an NHL team, but was signed as a free agent by the Philadelphia Flyers on the eve of his second junior season. However, his NHL career began with the Washington Capitals. His best NHL season came in 1992–93 while a member of the Hartford Whalers, when he scored a career-best 17 goals while earning 325 penalty minutes, which was the fourth-highest penalty minute total in the league that season.[citation needed]\n', '

In 1994, Kypreos was a member of the Stanley Cup champion New York Rangers. He made his final NHL stop with his hometown Toronto Maple Leafs. As a Maple Leaf, his career ended as the result of a concussion sustained in a fight with the Rangers\' Ryan VandenBussche in a pre-season game on September 15, 1997 when his face hit the ice after he was punched unconscious. After the injury, Kypreos suffered post-concussion syndrome and was forced to retire. He would finish his NHL career with 46 goals, 44 assists, 90 points, and 1,210 penalty minutes in 442 regular season games.\n', '

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