They entered the season as the two-time defending Stanley Cup champions.
[1] Divisions: CEN – Central, PAC – Pacific, NW – Northwest bold – Qualified for playoffs; p – Won Presidents' Trophy; y – Won division
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.