As it stands, the Oilers are five points behind the Ducks with one additional game played. With just nine games remaining, their odds of finishing first in the division are already pretty slim, but a loss would essentially end any chance of them finishing first.

It looked as if they’d have a chance to finish first in the division the last two seasons as well. However, a ton of injuries late in the 2024-25 season saw them finish nine points behind the Vegas Golden Knights. In 2023-24, the Oilers finished with 104 points, five fewer than the Vancouver Canucks, due to a 4-4-2 record in their last 10 games to end the season.

This may come as a shock, but the Oilers haven’t finished first in their division since 1986-87, despite making the finals five separate times since that season. Not only is that the longest division championship drought in National Hockey League history (both active and of all-time), but it’s also the longest active division championship drought in all the big four North American sports leagues.

Seriously, the next closest team in hockey is the New York Islanders, who last won it in 1987-88, while the Los Angeles Kings’ last won their division back in 1990-91. In the National Football League, the Cleveland Browns last won their division title in 1989, the lone streak in football that begins with “19”.

The National Basketball Association’s Charlotte Hornets have never won a division title, but their first season was in 1988-89, two seasons after the Oilers’ last division title win. And there are three teams in Major League Baseball who have droughts spanning back to the early 1990s, as the Colorado Rockies and Miami Marlins haven’t won their division since their inception in 1993, while the Pittsburgh Pirates have won their division title since 1992.

In this edition of Flashback Friday, we’ll take a look at the last time the Oilers won the division.

The Oilers’ 1986-87 season

The 1986-87 season saw the Oilers at their peak, as they went on to win their third of five Stanley Cups over seven years. The 1987 Stanley Cup Finals saw them take down the Philadelphia Flyers, which was fitting because it was their first opponent of the season, falling 2-1.

They followed that up with a 5-4 overtime victory over the Montréal Canadiens, but lost to their division rivals, the Winnipeg Jets, in their third game. Their first win streak came thanks to a 5-2 victory over the Québec Nordiques and a 4-3 victory over the Detroit Red Wings. After that game against the Red Wings on Oct. 17, the Oilers took the division lead.

Following that win streak, they lost twice and won once before embarking on a four-game winning streak. But a tie and a pair of losses put their lead in jeopardy, and on Nov. 14, 1986, the Oilers lost the division lead after going 5-4-1 in their last 10.

Just like the 2025-26 season, the Oilers took a few steps forward and one step back, regaining the division on Nov. 26, but they quickly lost it. Their season really began to take off in December, defeating the New York Islanders 7-1 on Dec. 3, before restoring their division lead on Dec. 5.

The Oilers never lost that division lead, as they went 10-2-1 in December 1986, with the lone tie being an impressive 8-8 game with the Kings. Although the Oilers never lost the division lead, it wasn’t quite secure yet. January saw the team split their first two games and on Jan. 8, they led the Calgary Flames by three points.

A 5-1 victory over the St. Louis Blues on Jan. 9 kicked off a five-game winning streak, with their long loss over a 12-game period being an overtime loss to the Buffalo Sabres on Jan. 18.

The next time the Oilers lost in regulation, Feb. 1, they had an 11-point lead over the Jets. Their February wasn’t particularly great, as they went 4-6-1, ending the month with a four-game losing streak. They ended February five points up on the Flames.

The Oilers went on a much-needed win streak, winning their first seven games in March, giving them a nine-point cushion over the Flames. Why was that important? Well, the Oilers lost both games of a home-and-home against the Flames, giving them a five-point cushion once again.

But by that point, the Oilers had two games in hand, going 5-2-1 to end the 1986-87 season, while the Flames went 2-3-1 over their next six. When the end of the season rolled around on April 5th, the Oilers won the division by 11 points. They didn’t break a sweat in the Campbell Conference, going 12-2 in the first three rounds, before defeating the Flyers in seven games.

Ryley Delaney is a Nation Network writer for Oilersnation, FlamesNation, and Blue Jays Nation. Follow her on Twitter @Ryley__Delaney.