2027 Stanley Cup Best Bets: Odds, Predictions & Picks
Don’t look now, but the 2026-27 NHL season is nearly underway! The first puck-drop is now less than a week away, and the pre-October start is thanks to the schedule expanding from 82 to 84 games. Those two extra matchups could make the difference between who makes the postseason and who doesn’t, so why not enjoy some 2027 Stanley Cup predictions? It’s never too early to do so, especially when there is significant plus-money value to be had!
Along with our best 2027 Stanley Cup picks, be sure to check out all of our NHL picks for Opening Night and beyond.
2026-27 NHL Stanley Cup Best Bet: Edmonton Oilers (+1000 at FanDuel)
Is it finally time? Ok, it’s a question that has been asked too many times at this point when it comes to 2027 Stanley Cup predictions, so the better question is this: did the Oilers finally secure strong enough goaltending to pair with the fire power of Connor McDavid and company? Well, the oddsmakers would suggest yes.
There are only a few teams with a price tag shorter than +1000, led by the Florida Panthers. Firstly, they’re in the Eastern Conference for Edmonton to avoid until the bitter end when daily 2027 Stanley Cup picks need to be locked in, and we may be seeing an inflated price simply due to the Tkachuk brothers being together. As for the biggest Western Conference threat, the Colorado Avalanche gave Cale Makar a record-setting contract, but they lost depth in the process.
So, about that aforementioned goaltending. We just saw the Carolina Hurricanes hoist the Stanley Cup, and Frederik Andersen is now in Edmonton. Of course, there is no guarantee here with his injury history and playoff inconsistency, but it’s still their biggest upgrade in quite some time.
After making the Stanley Cup Final in back-to-back years and then failing to do so, new head coach Mike Babcock can’t allow another step in the wrong direction. Instead, he needs to help the best 2027 Stanley Cup predictions hit for the Edmonton Oilers.
2026-27 NHL Stanley Cup Longshot: New York Rangers (+6000 at FanDuel)
If you’re sick of all the Connor McDavid drama and roll your eyes every time you hear “this is the Oilers year,” we get it. So, how about a 2027 Stanley Cup longshot pick? We could just fluster the entire country of Canada and talk about the Toronto Maple Leafs at +400, but instead, we’ve got our eyes on a different Eastern Conference squad.
It’s an even longer shot addition to our 2027 Stanley Cup predictions, but with a relatively recent Vezina Trophy winner between the pipes, we’ve seen crazier things happen. Elite goaltending can absolutely carry Stanley Cup playoff runs, and the chances of getting to the dance improved when they signed Pavel Dorofeyev. He was just part of the Vegas Golden Knights’ run to the Stanley Cup Final, scoring 35+ goals in back-to-back seasons.
Despite what their record would indicate, New York has the veteran leadership with Mika Zibanejad, Adam Fox and JT Miller while having added Marcus Pettersson. They’re a team that could be going under the radar; even if it’s not the 2023-24 Presidents Trophy season, the New York Rangers are the longshot pick from our best 2027 Stanley Cup predictions.
