Penguins vs. Oilers: Which team holds all-time bragging rights?

By Sean McIndoe, Daniel Nugent-Bowman and Sean Gentille

The Edmonton Oilers have a chance to make history this week, as they’ll look to stretch a win streak that currently stands at 16 games. They’ll try to get to 17 tonight in Vegas and then 18 on Friday in Anaheim, which would break the all-time NHL record currently held by the 1992-93 Pittsburgh Penguins.

In a way, that feels fitting. The Penguins and Oilers have felt like two teams connected for the better part of four decades. Wayne Gretzky gave way to Mario Lemieux as the league’s best player, around the same time that the Oilers dynasty was stepping aside for the Penguins. A generation later, it was Sidney Crosby passing the torch to Connor McDavid. And along the way, we’ve been able to debate Mark Messier vs. Jaromir Jagr, and Leon Draisaitl vs. Evgeni Malkin, and Paul Coffey vs., uh, Paul Coffey.

OK, great. So which team is better?

I don’t mean right now. I mean which team wins the all-time battle? The Penguins joined the league in 1967 and the Oilers arrived in 1979, and they’ve each won five Stanley Cups, tied for the most since they’ve both been in the league. They’ve both had legendary players. They both have devoted fan bases, and also plenty of other fans who can’t stand them.

Oilers vs. Penguins. Who you got?

That’s the question I asked two of our writers: Daniel Nugent-Bowman, who covers the Oilers, and Sean Gentille, who I’m told may be from Pittsburgh. I’m going to give them 10 categories and let them make the best case they can for their respective team. Then we’ll choose a winner.

Yes, there are other teams that could try to claim the modern crown, but this isn’t about them. Today, as we stand on the brink of win-streak history, it’s Oilers vs. Penguins in a one-on-one showdown. Let’s do this.

Championships

Both teams have won five, but not all Cups are created equal. Let’s hear the case that your five are better than their five.

DNB: The Oilers were the NHL’s last great dynasty, winning it all in five of seven seasons from 1984 to 1990. Included in that run were four titles in a five-season span. That kind of sustained dominance will never, ever happen again.

Case in point, we’re talking about the Penguins — whose five championships came over a 27-season span — as a comparable. That’s not even in the same stratosphere.

Gentille: Interesting. What happened after 1990? There are 40-year-old Oilers fans who don’t remember their Cups. In Pittsburgh, they connect generations. There are teenaged Pens fans from 1991 who a) got to experience it for themselves and b) got to experience it with their children 18 years later. And then they won two more. What’s more important than that?

McIndoe: We’re off to a great start, with Gentille already twisting the knife on Oilers fans.

Great players

This is the big one, with both teams being blessed with some of the all-time greats. But which team’s list is superior?

DNB: This…