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.