Darryl Sydor was drafted in the first round in the 1990 NHL Entry Draft by the Los Angeles Kings from the WHL's Kamloops Blazers. While a member of the Blazers, Sydor was named to the WHL West's First All-Star team in 1990, 1991, and 1992 and helped the team win the Memorial Cup in 1992.
Sydor made his NHL debut with the Kings in 1991-92 and the next year helped the team reach the Stanley Cup finals against the Montreal Canadiens. Even with Wayne Gretzky on their team Los Angeles fell to Montreal in five games. In 1994, Sydor was a member of team Canada when it won the gold medal at the World Championships.
After five seasons with the Kings, Sydor was traded to the Dallas Stars in 1996 and was an essential element on the blueline as the team won its first Stanley Cup in 1999. Sydor played in the 1998 and 1999 All-Star Games and has become one of the top offensive defenceman in the NHL.
In the summer of 2003 Sydor was acquired by the Columbus Blue Jackets and played in 49 games with the club before being acquired by the Tampa Bay Lightning just prior to the 2004 NHL All-Star Game. Upon his arrival with the Bolts, Sydor solidified the team's blueline and was instrumental in helping the team capture it's first Stanley Cup title and his second.
In order to clear salary, the Tampa Bay Lightning traded Sydor back to the Dallas Stars on July 2, 2006 in exchange for a 4th round draft pick. In his second stint with the Stars Sydor skated in 74 games tallying 21 points while averaging over 20 minutes of ice time per game. After returning the Stars, the unrestricted free agent signed with the Pittsburgh Penguins on July 2, 2007.
As a member of the Penguins, Sydor appeared in 77 games and his veteran leadership helped stabilize the club's blueline. However, only eight games into his 2008-09 season with the Penguins, the club dealt him back to Dallas for his third stint with the club on November 16, 2008, in exchange for Phillippe Boucher.