Craig Conroy played high school hockey at Northwood Prep School and in 1990-91, he enrolled at Clarkson University, scoring 29 points as an ECAC freshman. After scoring 19 goals and 36 points in his sophomore season, he had 33 points in his junior year. In 1993-94, Conroy led the ECAC with 40 assists and 66 points and was named an ECAC First Team All-Star. He was also named a NCAA East First Team All-American.
Conroy was selected 123rd overall in the 1990 NHL Entry Draft by the Montreal Canadiens. On February 15, 1995, he made his NHL debut in a 4-1 loss to the Whalers. He played five more games that season and scored one goal. The following season, he played seven NHL games.
On October 29, 1997, Conroy was traded with Pierre Turgeon and Rory Fitzpatrick to the St. Louis Blues for Murray Baron, Shayne Corson, and a fifth round draft pick. That season, he played 61 NHL games with the Blues and scored 17 points. In 1997-98, he was promoted to full time duty and scored 43 points in 81 games. He was also a finalist for both the Lady Byng and Selke trophies.
In 1998-99, Conroy recorded 34 points with the Blues. In the playoffs, he helped the Blues reach the second round for the second straight year. In 1999-00, he registered 27 points as the Blues won the Presidents' Trophy.
In 2000-01, Conroy was traded with a seventh round draft pick to the Calgary Flames for Cory Stillman and was one of the team's offensive and defensive leaders. After parts of four seasons in Calgary and helping the Flames reach the Stanley Cup final in 2004, only to lose a hard-fought seven game series to the Tampa Bay Lightning, Conroy signed as free-agent with the Los Angeles Kings in the summer of 2004.
Conroy's stint with the Los Angeles Kings lasted only a season and a half as the centreman was traded back to the Calgary Flames for Jamie Lundmark and a pair of draft picks. In his first game back with the Flames, Conroy tallied 2 goals ironically against the Los Angeles Kings.
On the international stage, Conroy was a member of USA's 2004 World Cup of Hockey Team, and it's 2006 Winter Olympic Team.