Parlays are the ultimate big-win chaser’s dream. The combined bets provide massive potential payouts on nominal wagers, and nearly every online sportsbook offers them. Though the odds are low for a given parlay to hit, the possible winnings are huge, and a handful of lucky bettors have cashed in some gargantuan parlay jackpots at legal sportsbooks worldwide.

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As stated, the question is a little vague however. I think its best you start on more of a completely well rounded approach on how to bet on sports in general. The UK Gambling Commission warned five online casinos in 2018 they could lose their licenses. They were not doing enough, the commission said, to stop criminals using their websites to launder money.

But before jumping into some of the craziest parlay wins on record, it helps to better understand the betting method, its upsides, and the inherent risk.

How Parlays Work

In simple terms, parlays are “all or nothing” bets. Parlays combine two or more individual bets into a single wager. This ramps up the odds so that a parlay pays much higher than any of the individual bets.

For example, I combined four bets with odds of -110, -110, +150, and +115 today on PointsBet, and the parlay payout came in at +1859. A $20 bet would pay more than $390.

Of course, there’s a catch. For a parlay to win, each individual bet must win. If you combine four bets into a parlay and one of them loses, you lose your bet even if the other three bets won. For that reason, parlays are risky bets, and most experts encourage you to steer clear.

On the other hand, casual bettors might enjoy making a weekly parlay every NFL Sunday or while any other league is in the thick of its season. There’s nothing wrong with making the occasional parlay bet as long as you acknowledge that your odds to win are low, similar to playing a slot machine.

Five Crazy Parlay Wins

Some bettors have beat the odds and been lucky enough to nab astronomical parlay wins in the past. Here’s a round-up of five amazing parlay wins.

The Three Sport Combo

Last year brought a huge windfall to one FanDuel sportsbook bettor who won on a $200 parlay combining 15 NBA, NFL, and NHL bets. The bet hit in November 2019 when all of the bettor’s moneyline wagers won for a payout of $229,276.

The moneyline bets boosted this wager over the edge for a massive win, because moneylines tend to offer longer odds if you pick the underdog. Whether it was sheer luck or educated guessing, this bettor came out on top.

The Charcuterie Parlay

In March 2019, sportsbooks were starting to take off in Mississippi on the heels of an August 2018 launch. March brought one noteworthy parlay win that featured a little bit of everything.

Rather than sticking to one type of bet, this bettor wagered $25 on a 20-leg parlay. The parlay was a veritable smorgasbord of bets and sports, including point spreads, moneylines, and totals. The wager covered a slate of Friday-night games across the NBA and NCAA basketball.

According to ESPN, the customer at BetAmerica sportsbook in Vicksburg, Mississippi’s Riverwalk Casino wagered on 14 favorites, three underdogs, and three “over” totals bets.

After a few close calls, the 20-leg bet won, netting the bettor a $104,412 win.

The Homecoming Special

In September 2020, a BetMGM customer raked in a $152,341 win on a $10 parlay.

The 11-leg bet featured five moneyline bets, five totals, and a single point spread wager (Duke +20.5). The majority of the bets predicted college football match-ups, but a few additional professional games sent the bet over the edge. The Rockets-Lakers under and the Yankees moneyline contributed to the win, resulting in a huge payday for the lucky bettor.

The 15-Leg NFL Slate

Amateur sports bettor Tayla Polia’s parlay success story is featured on countless lists just like this one, and for good reason. In 2015, Polia placed a $5, 15-leg parlay that included 14 point spread bets and one totals wager for the Steelers-Broncos matchup.

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To her surprise, Polia’s bet won and paid out 20,000-1 for a cool $105,000. She actually thought the bet had failed initially because the Giants lost their match-up. But Polia had bet on the team to cover, which they did, completing her parlay and netting her a huge win.

Root, Root, Root For The Home Team

In 2015, MLB fans worldwide witnessed history. For the first time since the league’s inception, all 15 home teams won their games on a single day.

One lucky bettor cemented his place in the story by predicting the event with a 15-leg parlay bet. The Ireland bettor had plenty of reason to celebrate proverbial Irish luck when his ~$78 bet, placed at William Hill’s sportsbook, won him $100,810.

Should I Place Parlay Bets?

You may see these wins and instantly open your sportsbook app to start placing a few parlays for yourself. Before you do, it’s important to note that these wins are the exception, not the rule. The sage advice from sports betting experts is to stay away from parlays.

However, it’s okay to place a parlay bet once in a while, especially if you feel confident about a select few match-ups. Parlays can be a fun way to get in on the action and invest yourself in the match-ups of the day. Just play responsibly and keep in mind that your chances of winning any parlay are slim.

Parlay Tips

If you’re planning to place parlay bets, there are a few tips to keep in mind.

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Less Is More

Sure, a 15-leg parlay is enticing, especially if the payout has four, five, or even six digits. But the more bets you include, the less likely you are to win. IF you’re interested in placing parlays, keep them simple at first. Combine two or three bets and see how they perform. If you’re lucky, you might win a few hundred dollars.

Favoritism Can Be A Benefit

Underdogs offer better payouts, but that’s only because they are viewed as less likely to win their match-up. If you’re building a parlay of moneyline bets, pay close attention to the odds. If one team is heavily favored to win, that might be the wiser pick.

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Carefully Consider Home Team Bets

Unless it’s the mid-90s and you’re placing Chicago Bulls bets every week, try to steer clear of home-team bets when you’re building a parlay. I’ve fallen victim to the trap many times–I place a 5-leg parlay bet that includes my Chicago Bears to win only to find a disappointing 4-1 parlay that loses me my initial bet thanks to a crushing Chicago loss.

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If you want to bet on your home team, keep that wager out of your parlays or risk disappointment.

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Point Spreads Even Out The Odds

Betting on point spreads gives you smaller individual payouts, but combining them into parlays can produce big potential wins. Point spreads even out the odds of a given match-up, giving the predicted underdog a chance to cover the spread even if they lose the match.