The 1998–99 NHL season was the 82nd regular season of the National Hockey League. The league expanded to 27 teams with the addition of the Nashville Predators. The Dallas Stars finished first in regular season play, and won the Stanley Cup championship over the Buffalo Sabres on a controversial triple-overtime goal by Brett Hull.

With the addition of the expansion Nashville Predators, the NHL realigned this year to a strictly geographic six-division structure (three per conference), erasing the last vestiges of the traditional Adams/Patrick/Norris/Smythe four-division structure abandoned in 1993–94. Other than the reassignment of Colorado to the Western Conference in 1995 due to its move from Quebec, the divisions' membership had remained static for five years although several franchises had relocated. As part of this realignment, the Toronto Maple Leafs moved from the Western Conference to the Eastern Conference. This put three of the Original Six teams in the Northeast Division (Boston, Montreal, and Toronto), and the three original cities of the NHL in the Northeast (Montreal, Ottawa, and Toronto).^{[1][2][3][4][5]}

The Maurice "Rocket" Richard Trophy for the most goals by a player in a season made its debut this year. The first winner was Teemu Selanne of the Mighty Ducks of Anaheim.

• Anaheim: The third and fourth jerseys from 1997 got new socks.
• Boston: The team wore a 75th-anniversary patch for their 75th season.
• Calgary: New Black Alternates introduced. Crest has its alternate Flaming-Horse Logo.
• Colorado: No updates in the regular season, but in the 1999 Playoffs, the Avalanche wore a CHS patch for the victims of the Columbine High School massacre on their left sleeve just above the number. The patch remained on the jerseys throughout the playoffs.
• Florida: The names on the back become vertically arched, and a navy blue alternate jersey is introduced. On that jersey, the panther is breaking a stick in half.
• Los Angeles: Jerseys Redesigned, Purple is Reintroduced.
• Nashville: white jerseys include a Blue triangle for the Crest, and the blue ones do not. The team wore an Inaugural season patch that would later become the team's alternate logo.
• New York Islanders: The jerseys reverted to its 1978–1995 design, retaining navy blue as its main color with a patch on the right shoulder featuring four diagonal stripes, symbolizing the team's four Stanley Cup titles in the 1980s.
• New York Rangers: White Lady Liberty Jerseys.
• Phoenix: The Coyotes introduce a new green alternate jersey, complete with a desertscape at the bottom and the sleeve ends
• St Louis: Alternates are retired and adopt a new color scheme
• San Jose: Alternates are retired and become the basis of the team's new uniforms.
• Tampa Bay: All-Star Game Patches for the 1999 NHL All-Star Game in Tampa.
• Toronto: Team wore alternate throwbacks and a patch to commemorate their final season at Maple Leaf Gardens.
• Washington: For the first few games, the Capitals wore a patch celebrating their 25th season in the NHL. The patch was worn on the upper right chest.

The 1998–99 season marked the retirement of Wayne Gretzky, the NHL's all-time leading scorer, who played his final three NHL seasons with the New York Rangers.^[6]

This was the final season that Fox televised NHL games in the United States. It was also the final season for the Toronto Maple Leafs at Maple Leaf Gardens, before moving to the Air Canada Centre in February and marked Toronto's first post-season appearance since the 1995–96 season. 1998–99 was also the final year that the Carolina Hurricanes played at Greensboro Coliseum; they moved to the brand-new Raleigh Entertainment and Sports Arena in Raleigh for the next season. The Colorado Avalanche played their fourth and final season at McNichols Sports Arena and would move to Pepsi Center the following season. The Los Angeles Kings played their final season at the Great Western Forum after 32 seasons before subsequently moving to the Staples Center for the next season.

In an effort to reduce the number of disallowed goals due to the skate-in-the-crease violation, regulatory reforms were implemented resulting the goal crease shape and size being significantly reduced.^[7] In spite of this regulatory change, goaltenders and defensive systems continued to dominate the league, as only two teams, the Toronto Maple Leafs and the New Jersey Devils,^[8] averaged more than three goals scored per game. In addition, no player reached the 50-goal plateau.^[9] A total of 160 shutouts were recorded for the second-straight regular season.^[10][11]

• List of Stanley Cup champions
• 1998 NHL Entry Draft
• 1998 NHL Expansion Draft
• 1998–99 NHL transactions
• 49th National Hockey League All-Star Game
• National Hockey League All-Star Game
• 1998 in sports
• 1999 in sports