1988 Stanley Cup playoffs

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 advantage during the playoffs thanks in part to Edmonton's struggles without Wayne Gretzky, who missed 16 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 New Jersey Devils made the playoffs for the first time since their move from Denver, 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.

Gretzky would go on to set NHL playoff records with 31 assists in 18 games and 13 points in the Stanley Cup Finals.

An exception to the 2–2–1–1–1 format was made during this year's Stanley Cup Finals after a power outage forced the cancellation of the original game four (see below).

This was the first time that a team representing the state of New Jersey qualified for the Stanley Cup playoffs.

This would be the last playoff series until the 2019 Eastern Conference First Round that the Islanders held home-ice advantage.

Washington won the only previous meeting in a three-game sweep in the 1984 Patrick Division Semifinals.

Washington overcame a 3–1 series deficit to advance to the Patrick Division Finals for the third time in five years.

Game seven ended when Dale Hunter scored at 5:57 of the first overtime period to complete the Capitals' comeback.

This was a rematch of the previous year's Norris Division Finals, which Detroit won in seven games.

This was a rematch of the previous year's Smythe Division Finals, which Edmonton won in a four-game sweep.

This was the second playoff meeting between these two teams and was a rematch of the previous year's Clarence Campbell Conference Final which Edmonton won in five games.

The series moved on to Edmonton, thus allowing the Oilers to win the Cup at home at Northlands Coliseum and complete the four game sweep.