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Monotony of Success – Part 2: How do the Oilers compare to others who reached back-to-back Stanley Cup Finals?

3 52
18.11.2025
In Part 1, I talked about why I decided to compare the 2025-26 Edmonton Oilers to the nine teams post-1990 that attempted to make the Stanley Cup Final for a third straight year. For more background and other notes, including just how bloody hard it is, read it here. This list compares Edmonton’s start through 20 games to these teams, while also looking at how they finished. After a preview where we looked at the 1992-93 Pittsburgh Penguins, we will glance at the eight other teams in the same position as these Oilers.

1998-99 Detroit Red Wings (lost in the second round)

  • DET record after 20 games: 12-8
  • Finish: 43-32-7, 93 points, third in West
The quest for a three-peat was on in Hockeytown, but the Red Wings knew that the Western Conference was the real challenge, since they had gone 8-0 through Stanley Cup Final games against Philadelphia and Washington.

Their core was to die for. Steve Yzerman, Brendan Shanahan, Sergei Federov, Igor Larionov, Nicklas Lidstrom, Slava Kozlov. Plus depth pieces like Kris Draper, Darren McCarty, and an old but still very productive Larry Murphy. The team had few holes. Their scoring was so spread out, no one achieved 30 goals, yet Detroit was one of the highest scoring teams in the league.

But the start wasn’t so hot. Their SC hangover saw them at .500 (8-8) after a loss to Calgary. As we’ll see a lot with these teams, they had a streaky year. December in particular was ugly, going winless in seven straight (0-6-1).

On trade deadline day, they bulked up. The big move was acquiring Chris Chelios on March 23 for two first-round picks and Anders Eriksson, enhancing their defence even more after signing Uwe Krupp in the off-season to help fill the void left by Vladimir Konstantinov. That wasn’t all. Wendel Clark, Ulf Samuelsson, and even Bill Ranford were added.

As these teams do, they won eight straight games at the end of March en route to a divisional title. However, they were 21 points back of first-place Dallas.

Anaheim stood no chance, soundly swept in the first round, setting up the third edition of Red Wings-Avalanche (Krupp’s former to boot). Colorado reverse-swept the Red Wings, going down 0-2 and winning four straight. The Avs would eventually lose to Dallas. Detroit got got.

2000-01 Dallas Stars (lost in the second round)

  • DAL record after 20 games: 12-5-3
  • Finish: 48-24-8-2, 106 points, third in West
The Stars came out of a tough Stanley Cup Final loss in 2000 and started to lose some of the innards of the champion core, but were still led by Mike Modano, Brett Hull, Joe Nieuwendyk, Sergei Zubov, Jere Lehtinen, and Ed Belfour.

Their start was pretty strong. After winning just one of their first four games, the Stars reeled off two five-game winning streaks.

Teams had a helluva time scoring on them, as they allowed just 187 goals against, second-best in the league. Dallas had 10 shutouts during the season.

Dallas defeated Colorado in back-to-back West Finals — these series are largely memory-holed but were absolute beauties — and there was a chance brewing they’d meet again. The Avs were hungry and had a huge first-place finish. The Stars........

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