It wasn’t that long ago that the Carolina Hurricanes hoisted the Stanley Cup, but the upcoming hockey season already lies just around the corner. The puck drops on the preseason in September before the regular season gets rolling in October, meaning there’s no better time than now to take a look at NHL futures and awards markets.
As teams hit the ice over the next few weeks, we’re diving into these betting markets to find the best bets and top picks. Here are the best longshots and sleeper picks on DraftKings Sportsbook to win the 2027 Stanley Cup.
2027 Stanley Cup Longshots: NHL Sleeper Picks and Futures Odds
Montreal Canadiens (+2200)
Technically speaking, the Canadiens are 10th in odds to win the 2027 Stanley Cup, so they’re in the NHL’s upper third when it comes to DraftKings Sportsbook’s bookmakers. After a season in which they made it to the Eastern Conference Final, it’s pretty clear they have a playoff-caliber core. They’re not a super-long pick by any means, but they bring an excellent blend of value and realistic upside here.
Montreal was arguably ahead of schedule with the deep playoff run over the summer. Five of the club’s seven top scorers from the postseason are currently 25 years old or younger. If you look at the regular-season production, eight of the 10 highest scorers are 26 or younger, too. This youthful core it is very talented, with plenty of room to grow as well. Lane Hutson is a Norris-type player, Cole Caufield is an elite finisher, and while he’s a smidge older at 28, Nick Suzuki is coming off a Selke-winning campaign himself. The Habs also have young up-and-comers in Juraj Slafkovsky and Ivan Demidov already performing like longtime pros. Goaltender Jakub Dobes performed pretty well with a 2.78 GAA and .901 SV% last regular season and notched 29 wins – in the playoffs, he caught fire early and stood on his head through the first couple of rounds.
The Canadiens do have some veteran talent in Philip Danault and Jake Evans, both of whom were key in the playoffs, and they just added winger Chris Kreider on a one-year deal. Small moves around the fringes like the latter are what’ll help this group ascend further in 2026-27. They’re only just entering the start of this window, so why not now? The value here looks great and this group should only improve with time, so perhaps they can turn some heads in the new season and capture a Stanley Cup before most believe they can.
Buffalo Sabres (+3000)
The Sabres started last season in poor fashion, but they caught fire when it mattered over the second half and went on to make history. They made the playoffs for the first time since 2011, but they didn’t just squeak into the field. Instead, they won their first division title since 2010 with 109 points and a 50-23-9 record in a very strong Atlantic Division.
Yeah, Buffalo fell to Montreal in seven games this past postseason and would likely have to meet the Habs again if neither of these teams win the division. Curse the playoff format, not me! But still, the Sabres won a series in pretty commanding fashion over the summer and are still on the come-up. Tage Thompson is coming off a point-per-game season and Rasmus Dahlin is one of the NHL’s best blueliners. Zach Benson has changed the lives of some Sabres fans and plenty of other talent from last year’s roster remains in place, both in the forward lines and in the defensive pairings. The loss of Alex Tuch hurts, but he was hardly a reliable producer in the playoffs anyways.
There is a big question mark surrounding Buffalo, but this team is a longshot to win the Stanley Cup for a reason. The goalie tandem of Ukko-Pekka Luukkonen and Alex Lyon showed incredible highs, but also some very low valleys last season – particularly in the postseason. Can one of them step up to perform when the lights are brighter? That’s what needs to be answered. But of course, it’s a long season and one Connor Hellebuyck hit the trade market a couple of weeks ago. After plenty of rumors suggesting the Sabres as a destination over the last year, maybe he’s the missing piece the roster needs.
