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The electrifying roar of the crowd, the sound of blades carving up the ice and the heart-stopping moments that define the Stanley Cup Finals – hockey fans know this thrill like no other. But what if we told you that the excitement doesn’t stop there? Imagine combining your passion for the game with the exhilarating world of sports betting, where dreams can be transformed into life-changing wins.


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With the NHL Playoffs all wrapped up, now’s the perfect time to take a look back at some of the biggest winning bets in Stanley Cup history at Bovada Sportsbook. From thrilling moneyline plays to long-term futures, we’ve seen some huge Stanley Cup payouts over the years. Keep reading as we count down the top 10 biggest Stanley Cup bets of all-time, celebrating the incredible wins that have forever etched their names in the pantheon of sports betting legends.

10. $15,000 to win $29,285

Back in 2019, the Boston Bruins and St. Louis Blues faced off in a thrilling seven-game Stanley Cup Final. While the Blues ultimately proved victorious in the series, this bettor cashed in on one of Boston’s Stanley Cup wins with a gutsy moneyline bet to the tune of $30,000. They may have lost the series, but the Bruins got the job done and earned this Bovada Sportsbook player scored a $29,285 payout to close out the NHL season.

9. $450 to win $15,300

That 2019 Stanley Cup victory by the Blues made money for a lot of hockey fans that season, as St. Louis came out of nowhere to claim their first Stanley Cup in franchise history. It appears there was one better who saw the writing on the wall and bet $450 at when the team was available at 33 to 1 odds to win the Stanley Cup. With the winnings totaling an impressive $15,300, this NHL futures bettor must have been laughing all the way to the bank!

8. $225 to win $15,529

The Blues’ surprising run in the 2019 Stanley Cup Playoffs surprised hockey fans everywhere and led to a number of big wins in the world of sports betting. This Bovada bettor turned an incredible profit on this Stanley Cup wager, locking in a Stanley Cup futures bet on St. Louis at nearly 70 to 1 odds. As we all know, this long shot panned out and turned a measly $225 investment into a massive $15,529 payout for this hockey bettor.

7. $1,000 to win $19,000

There’s no denying Alex Ovechkin’s greatness on the ice, but before 2018 many hockey experts doubted the Russian superstar’s ability to get the job done in the Stanley Cup Playoffs. That wasn’t the case with at least one hockey fan, as they wagered $1,000 on the Washington Capitals to win the 2018 Stanley Cup. With Ovechkin’s team locked in at a generous 18 to 1 odds, this bettor cashed in huge on the Capitals’ success with a $19,000 prize!

6. $2,667 to win $22,667

Back in 2020, before the team had won back-to-back Stanley Cups, there was still a number of question marks surrounding the Tampa Bay Lightning. Having been knocked out in the first round of the playoffs the year before, the Bolts were listed at +750 to win the Stanley Cup. It wasn’t easy, with the team having to go through Colombus, Boston and the Islanders before facing the Dallas Stars in the Final, but Tampa stuck it out and took home the 2020 Stanley Cup while this futures bettor took home $22,667 in winnings.

5. $10,000 to win $26,500

It looks like at least one bettor had a lot of faith in the Tampa Bay Lightning during the 2022 Stanley Cup Final. This user risked an even $10K on a Lightning moneyline wager against the Colorado Avalanche. Tampa was unable to win their third straight Stanley Cup, but they were able to pick up the win that night and that meant a $26,500 payday for this hockey fan.

4. $500 to win $28,000

As one of the biggest underdog teams in recent memory to win the Stanley Cup, the 2019 St. Louis Blues had long odds throughout most of the NHL’s regular season that year. In fact, St. Louis had the worst record in the entire NHL as late as January 3! As we all know, things turned around in a hurry for that team and they went on to defeat the Bruins and hoist Lord Stanley’s Cup. They probably weren’t the only ones celebrating that night – by locking in their Stanley Cup odds at over 50 to 1, this bettor earned their place on our list by turning a $500 bet into an incredible $27,500 payout!

3. $13,420 to win $28,858

The Montreal Canadiens enjoyed a memorable run to the 2021 Stanley Cup Final and although they eventually lost to the Tampa Bay Lightning in just five games, there was one Bovada bettor who still managed to cash in on the Habs. With the team trailing 3-0 in the best-of-seven series, this user bet $13,420 on the Canadiens to win Game 4 and avoid the sweep. Montreal managed to win that game in overtime, winning this NHL bettor a $28,858 payout!

2. $22,500 to win $37,499

It was in 2022 when the Colorado Avalanche took down the two-time defending Stanley Cup champion Tampa Bay Lightning. While the Avs were heavily favored towards the end of the series, that didn’t stop one bettor from laying down a massive moneyline bet on Colorado. This user risked $22,500 on the Avalanche, winning a cool $37,499 on the eventual cup winners and proving that betting on heavy favorites can be an effective strategy.

 1. $20,000 to win $46,000

Having reached the Stanley Cup Final for three straight years, the Lightning seemed to have made a lot of money for a lot of hockey fans. That team was on a mission in 2021 and this one bettor seemed to have known something the rest of the hockey world didn’t as they put down a colossal $20,000 bet on Tampa to repeat as Stanley Cup champions. The Lightning had no trouble reaching the final and the rest is history, with this brave Bovada bettor winning $46,000 for this great prediction.