Born in Grand Cache, Alberta, Dean McAmmond starred with the St. Albert Raiders before joining the WHL's Prince Albert Raiders in 1989-90. He was selected 22nd overall by the Chicago Black Hawks in the 1991 NHL Entry Draft and saw a bit of NHL action during the team's drive to the 1992 Stanley Cup final. The next year he returned to junior to play for the Raiders and the Swift Current Broncos.
Shortly after capturing gold with Canada's 1993 World Junior Team, McAmmond and Igor Kravchuk were sent to the Edmonton Oilers for Joe Murphy. The speedy young Oilers were a perfect venue for McAmmond to get comfortable with the NHL. During his first four years with the team, he gradually assumed greater responsibility and set career highs with 19 goals and 50 points in 1997-98.
McAmmond was included in a major exchange of young players between the Oilers and Blackhawks in March 1999. Other players in this deal included former first round draft picks Daniel Cleary and Chad Kilger. McAmmond was a solid two-way player for the Hawks in 1999-00 with 32 points and an impressive +11 plus/minus rating. His on ice performance during the regular season caught the eye of Team Canada officials and McAmmond was soon after named to Canada's 2000 World Championship Team for the second time in his career, the first time was in 1996. Prior to the March trade deadline in 2001, McAmmond was acquired by the playoff-bound Philadelphia Flyers to add depth. After only ten regular season and four playoff games, McAmmond rejoined to the Flames in 2001-02 and set a career high in goals with 20 and points with 50.
In 2002-03, McAmmond joined his fifth NHL team when he joined the Colorado Avalanche. The speedy forward played 41 games with the Avalanche before he was re-acquired at the trading deadline by the Flames. However, upon his return to the Flames, he was ruled ineligible to play for the remainder of the 2002-03 season by the NHL due to transaction violation by Calgary. Following a 30 point (17-13-30) season in 2003-04, McAmmond was acquired by the St. Louis Blues in the summer of 2005 after the 2004-05 NHL season was washed out.
Following his stint in St.Louis, the speedy centreman was signed as a free agent by the Ottawa Senators in the summer of 2006.
On the international stage, McAmmond represented his country at the 1993 World Junior Championship and twice at the World Championships (1996 and 2000).
In the days leading up to the 2009 NHL trade deadline McAmmond's time in Ottawa came to an end when he was sent to the New York Islanders along with a first round draft pick in exchange for forward Mike Comrie and defenseman Chris Campoli.