The 1998–99 Detroit Red Wings season was Detroit's 73rd season of operation in the National Hockey League. They entered the season as the two-time defending Stanley Cup champions.

Off-season

Regular season

Final standings

Playoffs

The Red Wings would enter the 1999 Stanley Cup Playoffs against the Mighty Ducks of Anaheim, and the series proved to be no contest. Detroit would sweep the Ducks in four games, setting up a rematch with their arch-rival Colorado Avalanche. Despite Detroit winning the first two games, they would go on to lose the next four consecutively, and were eliminated by the Avalanche.

Schedule and results

Regular season

Playoffs

Player statistics

Scoring

Goaltending

Awards and records

Awards

Milestones

Transactions

Draft picks

Detroit's draft picks at the 1998 NHL Entry Draft held at the Marine Midland Arena in Buffalo, New York.