Stanley Cup Betting Sites

Your Guide to Stanley Cup Betting Sites

The Stanley Cup Playoffs are one of the most exciting postseason tournaments in any sport. This makes for one of the more enjoyable marquee sporting events for betting.

In this article, we’ll take a look at which sites are best for Stanley Cup betting, how to sign up and how to claim the top bonus offers.

ByFrank Ammirante

Mar 13, 2024

NHL betting can sometimes get lost in the mix as it shares its regular season with the NFL and NBA, but there is no doubt that there is nothing more exciting in sports than the NHL playoffs.

After the Super Bowl has come and gone, most sports fans turn their attention elsewhere, and for many, the NHL is as good as it gets.

The US online sports betting market is constantly growing, which gives you a tough decision where to place your bets. Whether you watch all season or pick it up in the playoffs, NHL betting is growing in popularity.

We here at The GameDay want to help you choose the right online sportsbook to get you Stanley Cup bets in and take advantage of all the promotions that come along.

Benefits of Betting on the Stanley Cup Online

There are several benefits to betting online during the Stanley Cup playoffs. You’ll find a list of them below.

  • Convenience: You are able to place a bet from the comfort of your PC, laptop, or mobile device without going to a sportsbook and waiting in line
  • Welcome Bonuses: Betting online opens up opportunities for welcome bonuses, such as first deposit bonuses or risk-free bets
  • Promotions: You can also take advantage of any useful promotion available during the playoffs
  • Live Betting: Betting online is efficient, making it best for live betting, since you need to make a quick decision during a stoppage in play

Best Stanley Cup Betting Sites

Below you’ll find the best Stanley Cup Betting Sites. These sites will provide a user-friendly experience with promotions that put you in the best position to succeed. Let’s dive in:


DraftKings has a user-friendly app with every bet type you’ll need for Stanley Cup betting. This sportsbook enables users to put together same game parlays featuring player props. DraftKings offers new users with a First Deposit Bonus up to $1,000. Earlier this season, DraftKings had a promotion earlier in the season, where users can bet $1 and receive $100 in bet credits if either team scores a goal. You can bet that they’d have a similar promotion once the Stanley Cup playoffs begin.


FanDuel is similar to DraftKings in that it started off as a daily fantasy sports site and has moved into the sports betting space. The app is easy to use with a sleek interface. FanDuel has a comprehensive selection of player props. It is truly one of the leaders in player prop selection. Users can create same game parlays using these player props. FanDuel provides new users with a risk-free bet up to $1,000.


Caesars is one of the leaders in the sports betting industry. You’ll find every bet type you’ll need to enjoy Stanley Cup betting here. Caesars is offering its new users a bet match up to $1,001 as a welcome bonus. Caesars combines player props with event outcomes to provide users with pre-created same game parlays. For example, one might be “Pittsburgh Penguins to win" and Sidney Crosby to score a goal.”


Bet365 is another terrific choice as a Stanley Cup Betting site because it is easy to navigate. They have a detailed live betting system, where you can even place a live bet on a player prop. This is a novel concept that isn’t usually offered by other sportsbooks. Bet365 offers new users a first deposit bonus up to $500.


PointsBet has an innovative scoring system called “Points Betting,” where you risk more but with higher payouts depending on the outcome related to your wager. For example, if your bet wins by one, you win 1x your wager, but if it wins by three, you win 3x your bet. Conversely, if your bet loses by two, you lose 2x your bet, and so on. PointsBet had a useful promotion last postseason, offering new users the opportunity to bet their first $20 on the Stanley Cup Playoffs and receive $200 in bet credits if either team scores a goal.

How To Pick the Best Stanley Cup Betting Sites

It’s important to develop some criteria on how to pick the right sportsbook for Stanley Cup betting. You’ll find this list below:

  • User Interface: You want your sportsbook to be easily accessible with an organized layout.
  • Welcome Bonuses: It’s important to be able to have first deposit bonus or risk-free bets because they put you in a better position to succeed in Stanley Cup betting.
  • Promotions: Promotions are also useful because they increase your expected value. For example, you might earn bet credits just for placing a wager on Stanley Cup betting. This will help develop your bankroll.
  • Bet Types: It’s best if your sportsbook has a variety of bet types. Every sportsbook has moneyline and totals, but what does their player prop market look like? An expansive player prop market like FanDuel is preferred.
  • Payment Methods: You’ll want your sportsbook to provide several deposit and withdrawal methods to make the betting experience more convenient for you.

Best Stanley Cup Bets You Can Make

Betting on the Stanley Cup Playoffs can be difficult because of how unpredictable hockey can be. Let’s remember that back in 2019, the Tampa Bay Lightning, who had the best record in the league, got swept by the Columbus Blue Jackets, who squeaked into the playoffs. Be mindful of this when placing a bet on the Stanley Cup Playoffs. Let’s dive in to explore your best options:


Betting on Unders in the Stanley Cup Playoffs is usually go-to bet for NHL bettors because teams play a tight, defensive style, preferring not to take chances. You also see goaltenders get on ridiculous hot streaks where they’re seemingly unbeatable, like Carey Price in the 2021 playoffs. Betting on low-scoring games is the way to go in this market.

Player Props

Betting on player props helps to gain an edge in the Stanley Cup Playoffs market. One way to do this is to target elite players in good spots for production. For example, let’s say that the Edmonton Oilers are -200 favorites at home in a game with a 5.5-goal total. This gives them an implied total of three goals. The chances are high that Connor McDavid, the league’s perennial leading scorer (who usually averages 1.5 points per game), will produce in this spot. You can also do this with elite goal scorers who have gone cold because it’s only a matter of time before they find the back of the net.


Betting on a winner is the conventional way to go, but tread lightly on heavy favorites. Hockey is a sport that features a ton of upsets, so it’s inadvisable to pay a hefty price on the moneyline. I would try to find value on underdogs or parlay heavy favorites to reduce your risk.


Parlays are risky but profitable because they can lead to high payouts. I would recommend doing same game parlays, where you can correlate your plays. For example, if I pick Connor McDavid to go Over 1.5 points, I’ll include Leon Draisatl as well, since they play together.

Live Betting on the Stanley Cup

Live Betting is when you place a bet during a stoppage in play once the game has started. It is great for the Stanley Cup because this is a way for you to gain value after an early result.

For example, let’s say that you like the Toronto Maple Leafs to beat the New York Islanders. The Leafs are -200 favorites, which is too high of a price to pay. If you wait until after the puck drops and the Islanders take a 1-0 lead, you can now get the Leafs at around -125 to -150. This is a great way to use live betting to gain value.

You can also place a live bet if you have a sense of how the game is going. For example, let’s say that the Dallas Stars have a 2-0 lead on the Vegas Golden Knights. However, the Golden Knights are dominating play with tons of scoring chances. In this case, you might sprinkle a small bet on the Golden Knights to win because the potential payout is high.

Both of these live-betting strategies are useful, but make sure not to chase your original bet through this format. For example, let’s say you pick the Pittsburgh Penguins/Carolina Panthers Under 5.5 goals. Imagine the score is 2-2 after one period. Don’t continue to bet the Under to chase your original pick. It’s risky and could lead to a heavy loss.

Stanley Cup Betting Sites Bonus Offers

Welcome bonuses are highly useful because they put you in a better position to succeed in Stanley Cup Betting. You’ll find a detailed description of each type of bonus below.

No Deposit Bonus/Free Bet

A No Deposit Bonus is when bettors receive bet credits without requiring a deposit. This comes in the form of bet credits, usually ranging from $5-10.

Free Bets are given as loyalty rewards to experienced customers, usually to generate interest in a marquee sporting event, such as the Stanley Cup playoffs.

This type of bonus is useful for bettors to use as a trial run on an unfamiliar betting market or to take a shot on a longshot parlay with a high payout.

First-Deposit Bonus

A First-Deposit Bonus is when a sportsbook matches your first deposit up to a certain amount, usually ranging from $100-$1,000.

This means that if you deposit $200, you’ll receive $200 in bet credits. This is great to use to develop your bankroll.

Risk-Free Bet

A Risk-Free Bet is when you place your first bet without incurring financial risk because your sportsbook will reimburse your bet up to a certain amount if it loses. This is a great way to take a shot on an underdog or longshot parlay.

Bet & Get

Bet & Get is a bonus of bet credits, usually provided to new users once they bet on a specific betting market.

An example of this is the promotion provided by PointsBet last season, where bettors who put their first $20 on the Stanley Cup Playoffs would receive $200 in bet credits if either team scores a goal.

This is another useful promotion to help you build your bankroll.

You can legally bet online on the Stanley Cup in the following states:

  • Arizona
  • Colorado
  • Connecticut
  • Florida* (currently stopped due to legal issues, could continue in 2022)
  • Illinois (in-person sign-up required)
  • Indiana
  • Iowa
  • Michigan
  • Nevada (in-person sign-up required)
  • New Hampshire
  • New Jersey
  • Pennsylvania
  • Rhode Island (only one option)
  • Tennessee
  • Virginia
  • Washington D.C. (limited options)
  • West Virginia
  • Wyoming

Why You Should Avoid Offshore Betting Sites

It’s important to avoid illegal betting sites and just stick to the legal options. Here are some reasons why:

  • Illegal: Offshore online sportsbooks are not legal in the US. Only sportsbooks that are regulated by individual states are legal to bet on in the US Sportsbook market.
  • Unreliable: Offshore sportsbooks have unreliable customer support with limited payment methods and prolonged wait periods. You’ll also see some inconsistent odds compared to the rest of the betting market, perhaps a more expensive moneyline.
  • Lack of Promotions: They also don’t provide new users with welcome bonuses or useful promotions that help enhance the betting experience.
  • Limited Bet Types: Offshore sportsbooks have a more limited selection of bet types, especially with player props.

Choose More Than One Stanley Cup Betting Site

It’s important to choose more than one Stanley Cup Betting Site because this way you can take advantage of multiple bonuses, such as first-deposit bonuses and risk-free bets.

Take full advantage of the offer on the site you want to try first, and once you are done, you can move on to the next. These are one time offers, so make sure to maximize the free money offers as much as your current bankroll allows.

It’s also important to have multiple sportsbooks so that you can shop around odds. For example, one site might have Toronto Maple Leafs at -140, while another might have them at -130. This small difference matters a lot in the long run, so be sure to search for the best odds.


Frank Ammirante

Frank Ammirante is a Senior Sports Writer at The Game Day. Previously, he wrote for 4for4 Football and RotoBaller. Frank is a member of the Fantasy Sports Writer's Association while maintaining an active presence within the community. He has competed in industry contests like the Scott Fish Bowl, The Great Fantasy Baseball Invitational, and more. Frank will be making his debut in Tout Wars this year. He's got a diverse sporting background, but specializes in football and baseball.

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