Somewhat of a long-shot but one of my favorites: overtime of Game 4 of the 1996 semis between the hawks and avalanche, hawks lead the series 2-1. Roenick gets a breakaway but gets tripped from behind by Sandish Ozalinsh pretty blatantly. No penalty-shot given, not even a penalty. To me, it’s a pretty bad non-call. Avs end up winning the game and the series with Roy giving his famous “I’ve got my two stanley cup rings in my ears” chirp at roenick.
If Roenick gets a penalty shot there and scores (not a given obviously, it’s Roy, but Roenick did have success against him in that series) the hawks go up 3-1. Not insurmountable for the avs but not easy against the very good Hawks team (Roenick, Chelios, Belfour, Amonte, etc).
So let's say the hawks win that series, then they face Detroit in a WCF rematch from the previous year (detroit won in 5). I don’t really see the hawks overcoming the red wings here, so maybe the red wings end up playing against Florida which I imagine they win.
The red wings win a year early, which means they probably don’t trade for Shanahan to better match up with Colorado. Does Coffey still leave?
The Avs probably remain in contention the next few years but the a rivalry with detroit changes since there is no Lemieux hit on Draper and no revenge by McCarty and the Wings the next year in that famous brawl.
Maybe the next year it’s Colorado getting to the finals against Philly instead of Detroit.
Sadly I don’t think this changes anything for Chicago, since Bill Wirtz was a cheap bastard so Roenick is still gone the next year followed soon by Chelios.
Anyway, the play is at 29:45 here: