[citation needed] Kypreos struggled to score at the NHL level and immediately became known as an enforcer, a role he maintained throughout his pro career.

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.

His role was expanded in October 2014 when he became part of the new but revamped Hockey Night in Canada as an analyst after its parent, Rogers Media acquired the sole national television rights to the NHL in November 2013, until he departed in 2019.

Kypreos has also appeared on TSN as an analyst, notably when Hockey Canada announced the Canadian national team for the 2010 Winter Olympics.

Kypreos appeared as a pro hockey player, acting in a 1996 episode of the HBO program Arli$$ entitled "What About the Fans?".