The 1999 Stanley Cup playoffs, the championship of the National Hockey League (NHL), began on April 21, 1999 following the 1998–99 NHL season. The sixteen teams that qualified, eight from each conference, 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 last time all four WHA teams and teams with losing records (San Jose and Edmonton the 7th and 8th seeds in the Western Conference, respectively) made the playoffs.
Despite his team being eliminated Colorado Avalanche forward Peter Forsberg's postseason scoring totals with 24 points in 19 games, were not surpassed for the rest of the 1999 playoffs. This made him the first player to lead all playoff scorers despite not making the Stanley Cup Finals since the 1986 playoffs where Doug Gilmour and Bernie Federko each tallied 21 points in 19 postseason games for St. Louis who was also eliminated in the conference finals.
(3) Carolina Hurricanes vs. (6) Boston Bruins
This was the third playoff series between these two teams, with Boston winning both previous series. They last met in the 1991 Division Semifinals where Boston defeated the Hartford Whalers in six games. This was the first playoff series for the Whalers/Hurricanes franchise since moving to Carolina in 1997.
(2) Colorado Avalanche vs. (7) San Jose Sharks
Due to the Columbine High School massacre games one and two were played in San Jose, while games three and four were played in Colorado. Game 7 was to be played in Colorado had the Sharks won Game 6; however, the Avalanche defeated the Sharks in six games.
(4) Toronto Maple Leafs vs. (7) Buffalo Sabres
This was the first and to date only playoff series between these two teams. Toronto made their third appearance in the conference finals and first since losing to Vancouver in five games in 1994. Buffalo made their second consecutive and second overall appearance in the conference finals after losing to Washington in six games the year before.
In game one the Sabres backup goaltender Dwayne Roloson filled in for the injured Dominik Hasek. Leading 3–2 midway through the game Toronto appeared to be in control, but Stu Barnes tied the game for Buffalo at 14:37 of the second period. The Sabres went on to score twice in the third period on goals by Curtis Brown at 5:21 and Geoff Sanderson at 11:02, as Buffalo held on to win 5–4. In game two the Maple Leafs got two goals 18 seconds apart in the first period as Steve Sullivan scored at 10:28 followed by Sylvain Cote at 10:46. With just over ten minutes to go in the game Toronto held a 4–3 lead with Buffalo pressing. Steve Thomas' goal with 7:43 to go gave the Maple Leafs a 5–3 lead and Garry Valk sealed the 6–3 win with an empty-net goal at 19:30. With series tied at 1–1 the two teams traveled south to Buffalo for games three and four. Dominik Hasek returned for the Sabres in game three but it was the away team that netted the first goal as Maple Leafs forward Yanic Perreault scored at 16:08 of the first period. Buffalo was not to be denied and they scored three goals in the first 7 minutes and 38 seconds of the second period. Curtis Brown iced the game with an empty-net goal at 19:31 of the third period and the Sabres won 4–2.
Buffalo came out flying again in game four holding a 5–0 lead after two periods. Hasek's shutout bid was erased when Mats Sundin scored on a penalty shot at 6:59. Buffalo won the game 5–2, as Dominik Hasek made 31 saves in the victory. In game five the Sabres looked to advance to the Stanley Cup Finals for the first time since 1975. After a scoreless first period Steve Sullivan got Toronto on the board first, scoring a goal just 33 seconds into the second period. After goals by Curtis Brown, Kris King and Vaclav Varada the game was tied 2–2 after two periods. Erik Rasmussen broke the tie with a goal at 11:35 of the third period. Dixon Ward added a shorthanded empty net goal with 1:02 remaining as the Sabres went on to win 4–2 and take the series four games to one.
This was the first playoff series between these two teams. Dallas made their fourth conference finals appearance and second consecutive appearance after losing to Detroit in six games the year before. Colorado made their third conference final appearance in four years and their fifth appearance overall, they lost in six games to Detroit in 1997.
In game one the Stars jumped out to a 1–0 lead on Brett Hull's goal at 8:42 of the first period. The Avalanche came back to tie the game in the second period on Peter Forsberg's goal at 14:07. Valeri Kamensky scored the go ahead goal with 5:58 remaining in the game, as Colorado hung on to win 2–1. With the score tied at 2–2 in game two Joe Nieuwendyk gave Dallas a 3–2 lead with a goal at 11:52 of the third period. Mike Modano added a power-play goal with 3:32 remaining as the Stars won 4–2 to tie the series at 1–1. In game three Ed Belfour stopped all 34 Colorado shots he faced and Dallas won 3–0. The Avalanche came back in game four and led 2–1 with under five minutes remaining in the third period until Brett Hull scored at 16:07 to tie the score and send the game into overtime. In the extra period 22 year-old rookie Chris Drury scored at 19:29 to give Colorado a 3–2 win and tie the series at two games apiece.
Game five was the highest scoring game in the series as the two teams combined for 12 goals on just 56 shots. Chris Drury and Valeri Kamensky both scored twice as the Avalanche won 7–5. In game six Claude Lemieux got the Avalanche on the board first at 19:25 of the first period. The Stars responded early in the second on Jere Lehtinen's goal at 1:55. In the third period Jamie Langenbrunner scored twice at 6:49 and again at 17:15, 14 seconds later Richard Matvichuk scored to give Dallas a 4–1 lead which they hung on to. Ed Belfour stopped 26 of 27 Colorado shots (game six was the last NHL game to be played at the McNichols Arena as the Avalanche moved into the new Pepsi Center at the start of next season). The Stars dominated game seven building a 4–0 lead in the first 46 minutes and 18 seconds of the game. Mike Keane scored twice and Jamie Langenbrunner and Jere Lehtinen both had goals. Joe Sakic scored for Colorado with a goal at 13:58 of the third period. Dallas hung on and won the game 4–1 and the series four games to three. With the win the Stars advanced to the Cup Finals for the first time since 1991 when they were the Minnesota North Stars.