The Whalers and Toronto Maple Leafs made a trade on September 8, with Hartford acquiring Bill Root from Toronto for Dave Semenko. Root scored three goals and six points in 34 games with the Maple Leafs during the 1986–87 season.
On September 15, Hartford signed free agent Roger Kortko to a contract. Kortko was a member of the New York Islanders organization, and scored 16 goals and 46 points with their AHL affiliate, the Springfield Indians, during the 1986–87 season.
Wayne Babych announced his retirement from hockey on September 29. Babych appeared in four games with Hartford during the 1986–87 season, earning no points. He played a majority of the season with the Binghamton Whalers of the American Hockey League, scoring nine goals and 42 points in 78 games. During his NHL career, which began with the St. Louis Blues in 1978–79, Babych scored 192 goals and 438 points in 519 games while playing for the Blues, Pittsburgh Penguins, Quebec Nordiques, and the Whalers.
On October 5, the Whalers acquired Mark Reeds from the St. Louis Blues in a trade in which Hartford sent St. Louis their third round draft selection in the 1989 NHL Entry Draft. Reeds scored nine goals and 25 points in 68 games with the Blues in the 1986–87 season.
During the waiver draft, which was held on October 5, the Whalers claimed Brent Peterson from the Vancouver Canucks and Doug Wickenheiser from the St. Louis Blues. Hartford lost newly signed free agent Bill Root in the waiver draft to the St. Louis Blues, while Wickenheiser was then claimed by the Vancouver Canucks. Peterson, who remained with the Whalers, scored seven goals and 22 points in 69 games with the Canucks during the 1986–87 season.
[3]Note: GP = Games played, W = Wins, L = Losses, T = Ties, Pts = Points, GF = Goals for, GA = Goals against Note: Teams that qualified for the playoffs are highlighted in bold.
The Whalers opened the 1988 Stanley Cup playoffs against the Montreal Canadiens in a best-of-seven series. Montreal finished the regular season with a 45–22–13 record, earning 103 points, which placed them first in the Adams Division. The Canadiens finished with 26 more points than Hartford during the regular season. Previously, the Whalers and Canadiens met twice in the post-season, with Montreal winning both series. Their most recent match-up was during the 1986 Stanley Cup playoffs, as Montreal defeated Hartford with an overtime goal in game seven of the Adams Division final. The Canadiens went on to win the Stanley Cup that season.
The series opened on April 6 at the Montreal Forum in Montreal. Mike Liut got the start in goal for Hartford, while Patrick Roy started for Montreal. The Whalers scored the lone goal in the first period, as Randy Ladouceur scored 7:59 into the period, giving Hartford a 1–0 lead. In the second period, the Canadiens evened the game on a goal by Shayne Corson 2:54 into the period, followed by a goal by Bobby Smith less than two minutes later, giving the Canadiens a 2–1 after the second period. In the third period, the Whalers Richard Brodeur came into the game to play in goal, as Mike Liut was forced out of the game due to an injury. Despite the injury to their starting goaltender, the Whalers scored a quick goal, as Dave Babych scored 56 seconds into the period to tie the game 2-2. The Whalers took a 3–2 lead as Ron Francis scored a power play marker at 3:10. Montreal stormed back, as Chris Chelios scored on a Canadiens power play, evening the game at 3-3. The Canadiens regained the lead on a goal by Stéphane Richer midway through the period. Montreal held on for the 4–3 victory, taking a 1–0 series lead.
Game two was played the next night in Montreal, as Richard Brodeur would get the start in goal for the Whalers due to an injury to Mike Liut. Patrick Roy was once again in goal for the Canadiens for the second game. The Canadiens took a 1–0 lead on a goal by Brian Skrudland 5:30 into the first period. The Whalers tied the game midway through the period on a goal by Lindsay Carson. At 13:37, a goal by Chris Chelios gave Montreal the lead back at 2–1. Less than a minute later, Kevin Dineen tied the game for Hartford, as the game was tied 2–2 after the first period. The Canadiens retook the lead, as Gilles Thibaudeau scored 2:39 into the period, followed by a goal by Claude Lemieux at 10:59, as Montreal took a 4–2 lead. The Whalers Scot Kleinendorst cut the Canadiens lead to 4–3 with a goal at 12:52, as the Canadiens held the one goal lead after two periods. In the third period, Montreal scored three goals in a 2:38 span midway through the period, as Bobby Smith, Gilles Thibaudeau and Kjell Dahlin each scored, securing a 7–2 win for the Canadiens and a 2–0 series lead.
The series moved to the Hartford Civic Center for the third game on April 9, as Mike Liut returned in goal for the Whalers, while Patrick Roy made his third straight start for Montreal. The Whalers Stew Gavin scored an early goal, only 2:06 into the game, to give Hartford a 1–0 lead. The Canadiens tied the game midway through the period with a power play goal by Stephane Richer, as the score was 1–1 after the first period. The Whalers took a 2–1 lead with a power play goal by Sylvain Côté at the 6:31 mark of the second period. The Canadiens responded with three goals of their own before the period ended, as Craig Ludwig, Mike McPhee and Ryan Walter each scored, giving Montreal a 4–2 lead. In the third period, the Whalers Carey Wilson scored a power play goal 6:34 into the period, cutting the Canadiens lead to 4–3. Hartford couldn't manage to score another goal, as the Canadiens held on for the 4–3 victory, and took a commanding 3–0 series lead.
The fourth game was played the following evening, with both Mike Liut and Patrick Roy getting the starts once again in goal, as the Whalers faced elimination. The Canadiens took a 1–0 lead after Stephane Richer scored a goal at 3:22 into the first period. The Whalers quickly responded with a goal of their own, as Dean Evason scored 55 seconds later. At 8:29 of the first period, Dave Babych gave Hartford a 2–1 lead, which the Whalers took with them into the first intermission. In the second period, Stephane Richer scored his second goal of the game, which was the lone goal of the period, tying the game 2–2 after two periods. Only 59 seconds into the third period, the Whalers Dave Babych broke the tie, giving the Whalers a 3–2 lead. At 3:19, the Whalers Sylvain Côté took a four-minute high-sticking penalty, sending Montreal to the power play. The Canadiens scored twice on this power play, as Bobby Smith and Ryan Walter each scored, giving Montreal a 4–3 lead. At 11:20, the Whalers tied the game once again, as Kevin Dineen put the puck past Patrick Roy, tying the game 4-4. This was the start of a goal scoring outburst for Hartford, as Stew Gavin gave the Whalers a 5–4 lead with a goal 14:23. Kevin Dineen then scored a power play goal at 17:05, followed by a goal by Scott Young, his first career playoff goal, extending the Whalers lead to 7–4. Montreal's Gilles Thibaudeau scored a power play goal with 30 seconds left in the game, as Hartford staved off elimination with a 7–5 victory, cutting the Canadiens series lead to 3–1.
The series returned to Montreal for the fifth game on April 12, as Hartford once again was facing elimination. Richard Brodeur replaced Mike Liut in the Whalers goal, as he re-aggravated his injury. The Canadiens Brian Hayward got his first start of the series. Hartford scored the only goal of the first period, as Kevin Dineen scored midway through the period, taking a 1–0 lead into the first intermission. The Whalers Carey Wilson extended the lead to 2–0 with a goal at 5:40 of the second period. Montreal's Mike McPhee scored 31 seconds later, as Hartford held on to a 2–1 lead after two periods. In the third period, the game remained close, however, the Whalers Ron Francis scored an empty net goal with 16 seconds left in the period, securing the victory for the Whalers. This would be the last career post-season win for Richard Brodeur, who made 22 saves for the Whalers, as the Canadiens series lead was trimmed to 3–2.
Game six was back in Hartford on April 14, as both Richard Brodeur of the Whalers and Brian Hayward of the Canadiens got their second consecutive start. In the first period, the Canadiens Stephane Richer scored twice, as Montreal took a 2–0 lead after twenty minutes. In the second period, the Whalers Ray Ferraro scored a late period power play goal, cutting the Canadiens lead to 2–1. Both goaltenders continued to be sharp in the third period, as Hartford was unable to tie the game. The Canadiens won the game 2-1 and won the series 4–2, eliminating the Whalers from the post-season.