The 1988 Stanley Cup playoffs, the championship of the National Hockey League (NHL), began on April 6, after the conclusion of the 1987–88 NHL season. It concluded on May 26, with the defending champion Edmonton Oilers defeating the Boston Bruins to win their second straight Stanley Cup and fourth in five years.
The Presidents' Trophy winning Calgary Flames had home ice during the playoffs thanks in part to Edmonton's struggles without Wayne Gretzky, who missed a number of games due to injury. The Oilers, who had won the Cup in three of the previous four seasons, were still thought to have a good chance at repeating with Gretzky's return. The clash between the Flames and Oilers in the Smythe Division Final was highly anticipated.
The New Jersey Devils made the playoffs for the first time in their history, winning in overtime at Chicago Stadium on the season's final day to edge the New York Rangers for the Patrick Division's fourth spot. This was only the second time they made the playoffs including their Colorado and Kansas City days.
Gretzky set NHL playoff records with 31 assists in 18 games and 13 points in the Stanley Cup Finals.
The following teams qualified for the playoffs:
- Montreal Canadiens, Adams Division champions, Prince of Wales Conference regular season champions – 103 points
- Boston Bruins – 94 points
- Buffalo Sabres – 85 points
- Hartford Whalers – 77 points
- New York Islanders, Patrick Division champions – 88 points
- Washington Capitals – 85 points (38 wins, 9 points head-to-head vs. Philadelphia)
- Philadelphia Flyers – 85 points (38 wins, 5 points head-to-head vs. Washington)
- New Jersey Devils – 82 points
- Detroit Red Wings, Norris Division champions – 93 points
- St. Louis Blues – 76 points
- Chicago Blackhawks – 69 points
- Toronto Maple Leafs – 52 points
- Calgary Flames, Smythe Division champions, Clarence Campbell Conference regular season champions, Presidents' Trophy winners – 105 points
- Edmonton Oilers – 99 points
- Winnipeg Jets – 77 points
- Los Angeles Kings – 68 points
Montreal was the best team in the Wales Conference during the regular season.
This was the first and to date only playoff series between these two teams. This was the first time that a team representing the state of New Jersey qualified for the Stanley Cup playoffs. This was the first ever playoff series victory for the Scouts/Rockies/Devils franchise.
Washington overcame a 3–1 series deficit to advance to the second round for the first time in two years. Game seven ended when Dale Hunter scored at 5:57 of the first overtime period to complete the Capitals comeback.
Game six in Maple Leaf Gardens was future Hall of Famer Borje Salming's final playoff game in the NHL.
This was the twenty-third playoff series between these two teams. This was the fifth year in a row that these team met in the playoffs. Montreal had defeated Boston in the Division Semifinals the four previous seasons.
This was Boston's first playoff series victory against Montreal since 1943. Boston had lost the previous 18 playoff series between these two teams, an NHL record for most consecutive playoff series defeats to one team.
Patrik Sundstrom's eight-point effort in game three (3 goals, 5 assists) set a new Stanley Cup playoff record for most points in a single game.
In the Battle of Alberta the Oilers would claim the first sweep of the playoffs. In game two Wayne Gretzky scored the overtime winning goal short-handed.
This series also featured the infamous confrontation between Devils coach Jim Schoenfeld and referee Don Koharski after Game 3, when, during an argument in the tunnel after the game, Koharski tripped and fell, accusing Schoenfield of pushing him. Schoenfield famously responded, "Good, 'cause you fell you fat pig!" Then, he yelled "Have another doughnut! Have another doughnut!" The incident has since become part of NHL lore.
Schoenfeld was suspended by NHL president John Ziegler for Game 4, but the Devils received an injunction from a New Jersey court, allowing Schoenfeld to coach the fourth game. In protest, the officials scheduled to work that game in the Meadlowands refused to take the ice, forcing the NHL to scramble for amateur officials to call the contest. The injunction was lifted and Schoenfeld served his suspension during Game 5 in the Boston Garden.
The Red Wings were no match for the Oilers and were defeated in five games for the second consecutive year in the conference final.
Game four is well known for fog that interfered with the game and a power outage that caused the game to be canceled at 16:37 of the second period. This allowed the Oilers to win the Cup at home at Northlands Coliseum and complete the sweep in a rescheduled game four.