[1] Osgood spent the first part of his 17-year NHL career with the Red Wings, then the New York Islanders and the St. Louis Blues before returning to Detroit in 2005.

Osgood became the fourth goaltender to man the crease for Detroit that season alongside Tim Cheveldae, Vincent Riendeau, and Peter Ing.

Cheveldae, the team's primary starter, and a former All-Star, along with Dallas Drake, was traded to the Winnipeg Jets in exchange for veteran goaltender Bob Essensa and defenceman Sergei Bautin.

With the game tied 2–2 late in the third period, Osgood went to clear a puck around the boards, but it landed on Sharks forward Jamie Baker's stick, who then scored the winning goal.

Following the season, Detroit management felt the team needed a strong veteran goaltender with Stanley Cup playoff experience.

Osgood remained Detroit's primary goaltender until the summer of 2001, working alongside Ken Wregget and Manny Legacé before being put on waivers and picked up by the New York Islanders.

In the summer of 2001, the Red Wings acquired goaltender Dominik Hašek, a six-time Vezina Trophy winner, from the Buffalo Sabres.

After numerous attempts to trade Osgood, the Red Wings left him unprotected in the waiver draft, and the Islanders claimed him on September 28, 2001.

Osgood split playing time with Garth Snow for the 2001–2002 season and helped the Islanders to a playoff berth, where they lost a seven-game series to the Toronto Maple Leafs.

Although Osgood posted winning records for both seasons, the Blues did not advance past the playoff quarterfinals, losing to the Vancouver Canucks and San Jose Sharks, respectively.

Osgood also worked with rookie goaltenders Jimmy Howard and Joey MacDonald while Legacé recovered from knee injuries in late 2005.

With Osgood in goal, the Red Wings won their next nine playoff games in a row, defeating the Predators and sweeping the Colorado Avalanche as well as dealing the Dallas Stars a three-game deficit.

His save as time expired in Game Six sealed the Stanley Cup win for the Red Wings and for Osgood, who won his second championship as a starting goaltender.

[7] A combination of injuries and self-inflicted mental pressure adversely affected his game, to the point where late in the season he was essentially "sent home" for ten days by the Red Wings, in order for him to work with goaltending coach Jim Bedard and re-focus.

Although his 26 wins put him 10th all-time in the NHL by season's end, he finished with a GAA a full goal above what he had posted in 2007–08, and a save percentage in the bottom ten percent of all 45 goalies who played enough to qualify.

His drastically improved performance led to speculation that he was Detroit's leading candidate for the Conn Smythe Trophy as the Red Wings advanced to the Stanley Cup Finals for the second straight year.

[9][10] On September 9, 2013, it was announced that Chris Osgood was hired as a Red Wings game and studio analyst for Fox Sports Detroit, replacing fired-former teammate Larry Murphy.

[12][13][14][15] On August 30, 2016, Osgood, joined Red Wings' vice president Jim Devellano as part-owner of the Ontario Hockey League's Saginaw Spirit.