8 Insane Parlay Wins

Hundred Dollar Bills on Top of Sports Betting Tickets

The seasoned experts might advise against it, but multiple-leg parlays are one of the most exciting ways to bet on sports. It’s not often that you can turn $100 into $1,000 or more with just a few wins. The catch? It’s hard winning more than half of the games on your ticket, let alone all of them. In fact, the pros only win 52% to 53%. With that being said, when you read about these parlay winners you might think the risk is worth the reward.

1 – Beginner’s Luck

An admittedly novice gambler, Tayla Polia would quickly get her name in the record books with an NFL parlay that changed her life. In week 15 of the 2015 season, she decided to wager a modest $5 as a parlay on 15 separate bets (14 against the spread, one over/under). The odds for the particular bet were a long shot at 20,000 to 1.

Come Monday, she was $100,000 richer when all 15 games hit.

2 – Odd Parlay Prop

The Super Bowl is known for being a holiday for sports bettors, but for one unnamed gambler, Super Bowl LII was more like all the holidays rolled into one. Betting $15 on a nine-leg parlay full of prop bets, there was minimal risk, but winning was unlikely.

The odds were 400-1, but “odd” was the key to the winner’s night. He accurately predicted a high-scoring affair that was filled with odd numbers. The parlay was fulfilled as the game ended 41-33, and the odd numbered scores made for an even $6,000 payday.

3 – College Pays

Winning one parlay is hard enough, but one high-roller cashed in on an eight-teamer and a 10-teamer on the same weekend.

The New Jersey bettor wagered $1,200 across the two plays, which were comprised of mostly NCAA football games. Two NBA games were also snuck in at the end of the 10-team parlay. The odds for the two separate bets? 90 to 1 and 233 to 1.

Pen on Top of Parlay Bet

When the weekend was over, the book had paid out more than $300,000. Some questionable play calling led to a push in one of the games on the ticket, so the lucky winner missed out on even more cash. We can only hope he didn’t complain too much.

4 – A Nice Ring to It

Love, March Madness, gambling…few combinations could create a better story. Kevin Maselli of New Jersey had been in the process of saving up for a ring as a proposal to his girlfriend, Leah. The engagement loomed imminent. With the cost of rings soaring, $0.14 would soon go a long way in making the purchase.

Maselli had an interesting strategy when it came to sports gambling. He would make long parlay bets but would only wager 10 or 20 cents on each. He said they would hit occasionally, but with such a small amount wagered, the payouts weren’t huge.

During the 2019 NCAA Tournament, he bet a 14-leg parlay, choosing the winner against the spread and the over/under in seven separate games. When Auburn came back to win against Kansas, Charles Barkley wasn’t the only one yelling.

His unlikely $0.14 bet netted Maselli more than $1,300. Of course, he said he would put the money toward a ring.

5 – First Ever

On this list we’ve covered some unlikely wins with parlays up to 15 legs. This next winner took it to another level and completed the first 20-legger in the Vicksburg, Mississippi sportsbook’s history.

An unnamed bettor wagered $25 on a 20-game parlay that was a mix of leagues and bet types. All 20 games were either NBA or NCAAB games, and the bets were a combination of moneylines, spreads, and over/under.

How rare was the win? BetAmerica VP Alan Stremel said that it was the first 20-game parlay winner he’d ever seen. Other books said that they typically wouldn’t even offer the bet.

Now, the big reveal of how much the bet paid out on the initial $25—$104,400.

6 – The Favorite

The crazy thing about this particular win is that the lucky bettor only took favorites en route to an eight-leg parlay win. The wager encompassed eight college football NCAA games with lines ranging from -2 ½ to -37 ½.

After hitting on the first seven legs of the parlay, a series of miraculous events in the Stanford vs. Oregon game ensued. The Cardinal rallied from a 17-point deficit, helped in large part by an Oregon fumble as the clock winded down. Cardinal kicker Jet Toner (it just keeps getting better) sent the game to overtime with a field goal.

The rest is gambling history. Stanford managed to score a touchdown then forced an interception from Oregon’s Justin Herbert. Stanford wasn’t the only winner that night. A $366 bet cashed out at a little more than $61,000.

7 – Wrong Is Right

Sometimes, you just get lucky. One man placed a five-leg parlay bet at a Jamaican sportsbook on a series of soccer matches when he noticed something was off on his card. He had accidentally selected Roma over Barcelona in the last game of the day.

Upon recognizing his mistake, he attempted to cancel the bet but he didn’t make it in time and the card remained unchanged. This “mishap” ended up being rewarded with a more than $52,000 payout. As revered painter Bob Ross would say, “There are no mistakes, just happy accidents.”

8 – Wait, I Did What?

For some of us, when waking up after a long night of drinking, the money in our wallets disappear. Quite the opposite happened to one extremely lucky man on a visit to Las Vegas.

The story goes like this… Derek Bergee, after presumably several cocktails, wandered into a casino around 3:30 AM. A friendly visitor from Minnesota started chatting up Bergee and, as one thing led to another, Bergee ended up placing $100 on a four-leg parlay that was centered on Minnesota sports, including a college hockey matchup where he took a huge underdog over a traditional power.

Cashier Paying Out Parlay Bet

The hangover the next morning was undoubtedly eased, as all four parts of the reckless parlay hit, and the initial $100 was turned into $26,000 overnight. I’d be remiss if I failed to say that gambling at 3:30 AM while drinking heavily usually ends poorly. Proceed with caution.


While parlays, especially those with more than five or six games, are typically a long shot, this article proves that they can pay off. Some gamblers see great value in a bet where mere dollars can turn into thousands, but for most bettors it’s wasted cash.

While I would contest that sports betting involves more skill than luck, there’s no question that these winners were lucky more than anything else. If the math adds up, and you’re looking to roll the dice, pick out your 10 favorite games and let the chips fall where they may. As the New York lottery slogan says, “You just never know!”