This Saturday, April 18th, begins the chase for Lord Stanley’s Cup and a chance to hoist it when it is all said and done. All 2026 Stanley Cup Playoff teams have locked their spots in the tournament, but not all matchups are set in stone. Though, as it stands, the Eastern Conference has some pretty juicy matchups in store to get playoff hockey kicked off.
Stanley Cup Playoff: Canadiens vs Lightning
The first matchup breakdown is between the Tampa Bay Lightning and the Montreal Canadiens. During this year’s series, the teams split 2 -2, with the Lightning winning the first matchup on 12/9/25 by a score of 6-1. That by far was the largest margin of victory for either team against one another as Montreal lost the next one by one goal and then won the next two after that by 3 goals and 1 goal.
The most intriguing thing about this series is the series winner odds, as Tampa is -285 at FanDuel and Montreal is +230. Better yet, you can bet Montreal +1.5 on the series spread at -104 at FanDuel. Given the results of the season series, I would bet Montreal +1.5 no doubt, and while this may be a trap, I see it as being mispriced by Vegas.
Another bet I am looking at in this series is the series-leading goal scorer. I won’t be looking far into the list of odds for this one, as the top two listed at Caesars are Cole Caufield at +300 and Nikita Kucherov at +350. Each player leads their respective clubs in goals this season, and they do it almost at will. You can take one or the other, but I will throw a little on both!
Stanley Cup Playoff: Flyers vs Penguins
This next matchup is the famed ‘Battle of Pennsylvania’, between the Philadelphia Flyers and Pittsburgh Penguins. The Flyers find themselves in the playoffs for the first time since the 2019-2020 season, and the Penguins return to the tournament for the first time since the 2021-2022 season.
At the same time, both teams have some very bright, young talent and great veterans, which I believe could lead to a 6 or 7-game series. During the season series, these two split at 2 games apiece, and we saw the Flyers take their wins by 1 goal while the Penguins won each of theirs by at least 3 goals. Philly’s 6-3 and 5-1 losses came prior to the Winter Olympic break, and I believe since then that they have improved drastically, as in the last 9 games that the Flyers have faced fellow playoff teams, they are 8-1.
The first two bets I like in this series take me back to the well, where you can get the Flyers at +1.5 games in the series at DraftKings at -145. I foresee the Flyers keeping the series very close, if not winning it, and it won’t come easy against Pittsburgh, which leads into my next bet. You can get the series over 5.5 games at FanDuel at -205, which is a hefty price but could be a parlay piece. For a better price on this bet, check out DraftKings, where you can bet the exact number of games in the series. The series to go 6 games is +205, and to go 7 games is +215.
The third and last bet I have for the series is a longshot bet, but it’s worth a few bucks in my opinion. Egor Chinakov has been outstanding since coming over from Columbus, and in March and April combined, he had 22 points on the Penguins’ top line. With that being said, look at taking Chinakov to record 1 point each game at DraftKings at +2800 and Chinakov to lead the series in points at DraftKings at +3000.
Stanley Cup Playoff: Sabres vs Bruins
The Buffalo Sabres vs Boston Bruins season series may surprise you with its results and the current betting numbers for this series. Boston won 3 of 4 by scores of 3-1, 4-3, and 4-3. Currently, you can bet the Sabres to win the series at DraftKings at -175 or the Bruins at +145. So you may be wondering, what is going on here? I will tell you, it is another case of mispriced lines by Vegas. However, I like to play it safe, and I will take the Boston spread at +1.5 games in the series, but don’t be afraid to dabble in Boston as an outright winner.
Stanley Cup Playoff: Wild vs Stars
The Minnesota Wild vs Dallas Stars season series saw yet another split at two games apiece. Minnesota had a 5-2 win and a 2-1 win, while Dallas had wins of 5-2 and 5-4. As can be told by those numbers, this series is destined for a lot of scoring and a series to go over its total of 5.5. You can find that bet to be a bit pricey at -210, but again, check out DraftKings, where you can bet the series to 6 games at +200 or 7 games at +210.
What lies ahead
To put it simply, this year’s tournament will be electric. It is filled with star-studded talent, and no team gives me definite win vibes. The cup is anyone’s to take if they want it bad enough, so tell everyone you know. Some of the best hockey this season will be played from now until June; you can count on that.
