Fedorov was drafted by the Detroit Red Wings in the 1989 NHL Entry Draft, fourth round, 74th overall. In his pre-NHL days, he played for CSKA Moscow on a line with future NHL superstars Pavel Bure and Alexander Mogilny and was drafted in the same year as Bure and a year after Mogilny. In 1990, while CSKA Moscow was in Seattle for the Goodwill Games, Fedorov quietly slipped out of his hotel room and onto an airplane bound for Detroit. Thus, he became one of many NHL stars to have defected from the Soviet Union to play in the NHL.

 

During the 1993-94 NHL season, Fedorov won that year's Hart Memorial Trophy (being the first European-trained player to do so), the Frank J. Selke Trophy, and the Lester B. Pearson Award. He finished second in scoring behind Los Angeles' Wayne Gretzky with 56 goals and 120 points.

Fedorov won another Frank J. Selke Trophy in 1996, after compiling another 100-point season with 39 goals and 107 points. One year later, he was a member of the Red Wings' first Stanley Cup championship team since 1955, contributing 20 points in 20 playoff games for Detroit.

 

After a lengthy holdout to start the 1997-1998 season, Fedorov, a restricted free-agent, signed an offer sheet with the Carolina Hurricanes worth up to $38 million (with bonuses). The Red Wings matched the offer on February 26, 1998, ending Fedorov's holdout. The offer broke down as: $14 million for signing, $2 million for 21 regular season games, $12 million for the team reaching conference finals. $28 million for 43 total games in 1997-98 is the largest single season amount paid to an NHL athlete. Fedorov helped the Red Wings win their second consecutive Stanley Cup that year.

 

On February 18, 1999 Fedorov announced that his entire base salary for the 1998-99 season, $2 million, would be used to create the Sergei Fedorov Foundation, a charity to assist Detroit area children. During the 1990s, Fedorov was third in playoff scoring, with 134 points behind only Jaromir Jagr (135) and Mario Lemieux (136). He is only the 3rd player in NHL history to have four consecutive 20+ point playoff campaigns. (Mike Bossy and Bryan Trottier are the other 2.)

Fedorov won a silver medal with Russia in the 1998 Winter Olympics in Nagano, and a bronze medal in the 2002 Winter Olympics in Salt Lake City.

 

In the 2003 offseason, Fedorov signed with the Mighty Ducks of Anaheim. Fedorov remained with Anaheim between 2003-2005. It was with the Ducks that Fedorov picked up his 1,000th point, becoming the first Russian-born and fifth European-born player to do so. In an unanticipated move, he was traded to the Columbus Blue Jackets on November 15, 2005. Fedorov, as a Blue Jacket, also played his 1,000th NHL game on November 30, 2005, becoming the 13th European-born player to reach 1,000 NHL games and the 205th player overall to do so.

 

In a 2006 interview, former Red Wing head coach Scotty Bowman said, "[Fedorov was] one of my favorite players as a coach because he can do anything [asked of him on ice]." Bowman coached nine of Fedorov's thirteen seasons with Detroit. During the late 1990s, Bowman experimented by using Fedorov on defense and pairing him with Larry Murphy. The Red Wings senior vice-president Jim Devellano said, "I’m convinced if we left him there, he’d have won a Norris Trophy". Although he was effective playing defense, Fedorov stated that he would rather play up front. This has not prevented current Blue Jackets head coach Ken Hitchcock from moving Fedorov back to defense, however, as Hitchcock, who took over the team mid-season, prepares for next season.

 

The acrimony created during his 1997-98 holdout led to some hard feelings among some Wings fans, and those feelings were only intensified when he signed his free-agent contract with Anaheim after the Wings lost the first round of the playoffs that year to Anaheim. Fans seemed to take the fact that Anaheim signed him for less than the Red Wings offered him as a personal slap in the face. Fedorov has since become the most consistently-booed player at Joe Louis Arena when his team comes in to play the Red Wings, as fans jeer him every time he touches the puck. Even so, he is fourth all-time in nearly every offensive category in Red Wings history behind Gordie Howe, Steve Yzerman and Alex Delvecchio. Only Howe, Yzerman, Delvecchio and Nicklas Lidstrom played more games as a Red Wing.