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 four-division structure (Adams/Patrick/Norris/Smythe) abandoned in 1993–94. Other than the necessary reassignment of Colorado to the Western Conference in 1995 due to its two-thousand mile (over 3,200 km) move west 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, Toronto), and the three original cities of the NHL in the Northeast (Montreal, Ottawa, Toronto).
In an effort to reduce the number of disallowed goals due to the skate-in-the-crease violation, the goal crease size was significantly reduced. In spite of this, goaltenders and defensive systems continued to dominate the league, as only two teams, the Toronto Maple Leafs and the New Jersey Devils, averaged more than three goals scored per game. In addition, no player reached the 50-goal plateau. A total of 160 shutouts were recorded for the second-straight regular season.
The teams split the first two games, held in Dallas, then split the following two games in Buffalo. In the fifth game, Dallas shut out Buffalo to put the Sabres on the brink of elimination. Game six was held in Buffalo and it went to triple-overtime before being decided on a controversial goal scored by Brett Hull while he was in the goal crease.Joe Nieuwendyk of Dallas was awarded the Conn Smythe Trophy as the playoffs' most valuable player.
March 23, 1999: Nashville traded RW Blair Atcheynum to St. Louis for a sixth-round pick in the 2000 Entry Draft.
March 23, 1999: Calgary traded D Chris O’Sullivan to NY Rangers for D Lee Sorochan.
March 23, 1999: Detroit traded G Kevin Hodson and San Jose’s second-round pick in the 1999 Entry Draft (previously acquired) to Tampa Bay for LW Wendel Clark and Detroit’s sixth-round pick in the 1999 Entry Draft (previously acquired).
March 23, 1999: Washington traded C Dale Hunter and a third-round pick in the 2000 Entry Draft to Colorado for a second-round pick in the 1999 or 2000 Entry Draft.
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