To be honest, I'm changing my vote to Edmonton... and not because I'm a fan (which I am but I originally went PIttsburgh)... here is why!
Pens joined the NHL in 1967
Oilers joined in 1979
So Pen's have a 12 year advantage
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They are tied in cups
Oilers have been in the finals 8 times to 6 times in 12 less seasons.
I think it's very close but that broke it for me after my initial Pen's vote.
I'd love to see a similar pole of teams that have entered the league at same time and have had similar tenures in NHL as that is why I left out Boston and Chicago...
Although, to that end, they had a massive head start on both teams and have 1 more cup then Oilers and Penns despite playing in 6 team leauges and having several decade leads on the record books.
And last one... when Pens joined there were 12 teams
When Oilers joined there were 21 teams
Player wise I'd say Gretzky, Messier, Kurri, McD, Drai are on a simlar plane with Jagr, Lemieux, Malkin and Crosby
Pens have made the playoffs
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37 out of 56 for a 66% playoff ratio
Oilers have made the playoffs
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26 out of 44 for a 59% playoff ratio