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 and in 1987-88, he co-led the Whalers with 25 goals and was voted to play in his first mid-season All-Star Game.
On November 13, 1991, Dineen was traded to the Philadelphia Flyers where he got to play under head coach-dad Bill Dineen through 1992-93 and was the team captain for the 1993-94 season. In 1992-93, Dineen finished the season with a career-high six-point game against the Sabres and his fifth career 30-goal season.
In the shortened 1994-95 season, Dineen was a runner-up for the Masterton Trophy and helped the Flyers make the playoffs for the first time in six years as the team advanced all the way to the Eastern Conference Finals.
Midway through the following season, Dineen was traded back to the Whalers, and in 1996-97, won his second Whalers' True Grit Award as he led the team with five game-winning goals. Dineen and the Whalers moved to Carolina in 1997-98 and played two seasons with the Hurricanes before signing as a free agent with the Ottawa Senators in 1999-00.
After only one season in Ottawa, Dineen was claimed by the Columbus Blue Jackets in the 2000 NHL Expansion Draft and went on to play two seasons in Columbus before retiring from the game four games into the 2002-03 season.
Throughout his career Dineen represented Canada at the 1984 Olympic Winter Games in Sarjevo and again in 1985 at the World Championships where the team won a silver medal. A member of Team Canada that beat the Soviets in the 1987 Canada Cup tournament, Kevin Dineen went on to play over 1,188 games in the NHL.