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The 1999 Stanley Cup playoffs, the playoff tournament of the National Hockey League (NHL), began on April 21, 1999, following the 1998–99 NHL season. Prior to the season, the league realigned its teams into six divisions. Thus, the 16-team, conference-oriented playoff format used since 1994 was modified accordingly to allow each of the division winners to automatically qualify, along with five other teams from each conference. The teams played best-of-seven series for conference quarter-finals, semi-finals and championships, and then the conference champions played a best-of-seven series for the Stanley Cup. This was the first time since 1987, and only time until 2020 where all former WHA teams clinched the playoffs.
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