Chris Osgood was drafted 54th overall in the 1991 Entry Draft by the Detroit Red Wings. On October 15, 1993, he made his NHL debut against the Maple Leafs. On October 23, he earned his first win against the Kings. That season, Chris shared goaltending duties first with Tim Cheveldae and then Bob Essensa after his team made a trade with the Jets. Chris played 41 games and posted a 23-8-5 record with a 2.86 goals-against average as the team won the Central Division title. In the shortened 1994-95 season, Chris went 14-5-0 in 19 games and shared goaltending duties with Mike Vernon as the Red Wings again won the Central Division title. In the playoffs, Chris played in two games as the Red Wings won the Clarence Campbell Bowl in the Western Conference finals before losing to the Devils in the Stanley Cup finals.
In 1995-96, Chris paced the league with 39 wins as the Red Wings won both the Central Division title and the Presidents' Trophy with a league-record 62 wins. Chris went 39-6-5 in 50 games and posted a 2.17 GAA with five shutouts as he and Vernon shared the Jennings Trophy. Chris played in the mid-season All-Star Game and was a year-end Second Team All-Star. He also strung together a team-record 21-game unbeaten streak from January 10 to March 27. On March 6 of that string, he scored a goal against the Whalers. In the playoffs, Chris played 15 games as the Red Wings reached the Western Conference finals before losing to the Avalanche.
In 1996-97, Chris went 23-13-9 in 47 games and posted a 2.30 GAA with six shutouts. During the season, he played in his second All-Star Game. In the playoffs, he played in two games as the Red Wings won the Clarence Campbell Bowl and the Stanley Cup. It was the Red Wings' first Stanley Cup victory in 42 years. In 1997-98, Chris went 33-20-11 in 64 games (his new goaltending partner was Kevin Hodson) and posted a 2.21 GAA with six shutouts. That year, he played in his third-straight All-Star Game. In the playoffs, he led the league with 22 games, 1361 minutes played and 16 wins as the Red Wings again won both the Clarence Campbell Bowl and the Stanley Cup.
In 1998-99, Chris went 34-25-4 in 63 games as the Red Wings won the Central Division title. That season, his goaltending partners were Norm Maracle and Bill Ranford. In the playoffs, Chris was undeafeted in the opening round before missing four games in the second round with a sprained knee (they were eliminated that round). In 1999-2000, Chris shared goaltending duties with Ken Wregget and Manny Legacé and went 30-14-8 in 53 games. Chris posted a 2.40 GAA and six shutouts. In the playoffs, he led the Red Wings to the second round with a 1.97 GAA.
In 2000-01, Chris shared goaltending duties with Legacé as the team won the Central Division title. Chris posted a 25-19-4 record with a 2.69 GAA in 62 games. On October 28, Chris stopped 14 shots by the Blue Jackets for his 200th career win.
On September 28, 2001, Chris was claimed on waivers by the New York Islanders. On October 20, 2001, the night the Islanders retired Bryan Trottier's sweater number 19, Chris made 35 saves in a 2-2 tie with the Sharks.
