2021 Stanley Cup Playoffs First Round Series Odds, Preview, and Picks

• Odds are posted for all eight Stanley Cup first-round playoff series
• The Colorado Avalanche (-335) are the biggest favorites to advance through their series against the St. Louis Blues
• As far as underdogs, the New York Islanders (+121) have the shortest odds in their set facing the Pittsburgh Penguins

The theory in the NHL Stanley Cup playoffs is that the first round is the toughest series to win for favorites. The pressure on a top contender in the Stanley Cup odds to not throw away an excellent regular season by virtue of an opening-round exit from the postseason is immense.

In last year’s NHL postseason, four of eight qualifying-round series ended in upsets. There were two more upsets among the eight first-round series.

That being the case, should you go all-in on underdogs? No, but recognize that there will be upsets and wager accordingly.

2021 NHL Playoffs First Round Series Odds

Odds as of May 14th

The 2021 Stanley Cup playoffs get underway Saturday at 7:15 PM EST on NBC, with the Washington Capitals playing host to the Boston Bruins in an East Division matchup.

Leafs-Habs Have History

Hard to believe considering the history between these two franchises that it’s been 42 years since they met in a playoff series. There’s a misnomer being reported that every time Toronto and Montreal face each other in the playoffs, the series winner also wins the Stanley Cup. Sorry to report that it’s not 100% true.

In 1925, Montreal beat Toronto to win the NHL title. The Canadiens then lost the Stanley Cup final to the Victoria Cougars back in the days when more than one major league was in competition for the trophy.

Leafs 🆚 Canadiens this season

TOR: 7-2-1 … 34 goals

MON: 3-6-1 … 25 goals

— Mark Masters (@markhmasters) May 12, 2021

However, in their other 14 meetings, the Cup-winning trait holds true. Each team won seven of those 14 series and took the Cup. In fact, not only did the Leafs win their most recent Cup by beating the Habs on May 2, 1967, that’s also the last time Toronto beat the Canadiens in a playoff game.

That figure is going to change this spring. The Leafs will win their first postseason series since 2004. Montreal is good enough to stay with the Leafs for a time, and Habs goalie Carey Price can probably steal a game, but Toronto is too deep to be held off for an entire series.

Don’t waste your time betting the Leafs at -275 in the first-round series odds, though. Wager on one of the series props, such as Toronto to lead 2-1 after three games (+130), or Toronto to win in six games (+400).

Pick: Leafs to win in 6 games (+400) 

Penguins Alone With The Islanders

It’s been a spectacular campaign for the Pittsburgh Penguins. They’ve overcome an incredible string of injuries to win the East Division. And the prize for that perseverance is a date with their worst nightmare, the New York Islanders.

If you’re a Penguins fan, there are a plethora of reasons to be frightened. These two teams have met four times in the postseason. The Isles won three of the series.

Penguins vs. Islanders

Mark your calendars! 🏒 pic.twitter.com/pj5N05qTOp

— Tribune-Review Sports (@TribSports) May 13, 2021

Two years ago, the Isles utilized their smothering defensive system to sweep the Pens, much in the manner that Montreal eliminated Pittsburgh in last year’s qualifying round. Islanders coach Barry Trotz has beaten Pittsburgh the last two times he’s faced them in the playoffs.

Pick: New York Islanders (+121)

Vegas Not Wild About Matchup

The Vegas Golden Knights are the second betting choice to win the Stanley Cup at odds of +550. Yet looking at the club’s recent history in big games, there must be cause for concern with this team.

For the first time, the Wild and Vegas Golden Knights will meet in the playoffs.

Wild are a league-best 11-2-3 against them all-time, 5-1-2 this season.

— Michael Russo (@RussoHockey) May 14, 2021

With the West Division title on the line, they lost 2-1 to the Colorado Avalanche. Last year, they blew a 3-1 lead to Vancouver before saving face with a Game 7 triumph. In 2019, Vegas lost in seven to San Jose after leading the set 3-1.

The Minnesota Wild are the Golden Knights’ kryptonite. Minny has won 11 of 16 all-time and five of eight this season from Vegas. +190 odds is great value on the Wild to win their first-round series.

Pick: Minnesota Wild (+190)