These events occured in 1999 in the world of hockey:
- Art Ross Memorial Trophy as the NHL's leading scorer during the regular season: Jaromir Jagr, Pittsburgh Penguins
- Hart Memorial Trophy for the NHL's Most Valuable Player:
- Jaromir Jagr – Pittsburgh Penguins
- Stanley Cup – Dallas Stars defeat the Buffalo Sabres 4 games to 2, Conn Smythe Trophy – Joe Nieuwendyk. The Stars became the first team from the Southern United States to win the Cup.
- World Hockey Championship
- Men's champion:Czech Republic defeated Finland
- Junior Men's champion: Russia defeated Canada
- Women's champion: Canada defeated the United States
- NCAA Men's Ice Hockey Championship – University of Maine Black Bears defeat University of New Hampshire Wildcats 3–2 in overtime
- May 3: Carolina Hurricanes defenseman Steve Chiasson is killed in a car accident while intoxicated just hours after Carolina had been eliminated from the NHL Playoffs by the Boston Bruins.
- May 30th: The Mississippi Sea Wolves win the Kelly Cup by defeating the Richmond Renegades 4 games to 3 in the Kelly Cup finals.