Kevin Dineen played one year of Junior B hockey with the Toronto St. Michael’s team, then played two years with the University of Denver where scored 26 goals in two seasons. He turned pro in 1984-85 with the AHL’s Binghampton Whalers and scored 15 goals in 25 games before making his NHL debut during the season.

Selected in the third round of the 1982 NHL Entry Draft by the Hartford Whalers, Kevin Dineen made his NHL debut on December 3, 1984 against the Montreal Canadiens. It was against those same Canadiens less than two weeks later that Dineen scored his first NHL goal against Doug Soetaert finishing his his rookie season with 25 goals.

In just his second year with the Whalers, Dineen helped the club improve 15 points in the standings and advance to the playoffs for the first time in five years. In 1985-86, the Whalers lost in a game-seven overtime thriller against the eventual Stanley Cup champions from Montreal. In 1986-87, the Whalers followed up a strong post-season with a team best 43 wins and 93 points to win their first regular season Adams Division title. Dineen led the Whalers with 40 goals and won the Shawmut Bank Favourite Whaler Award. He represented the NHL at the Rendez-Vous ‘87 series against the Soviet All-Stars in February. In 1987-88, Dineen co-led the Whalers with 25 goals and was voted to play in his first mid-season All-Star Game.