Small Bets That Paid Off Big Time

Like any form of gambling, the world of sports betting has its winners and losers. What are the biggest sports betting wins of all time you may ask? Without going into specifics, we can confidently say the biggest pots have gone into seven-figure territory. Some of these seasoned gamblers bet in the hundreds and even thousands to win that kind of money, which also speaks to how much sports betting has impacted the economy. Something equally impressive, however, are the novice gamblers who placed small bets and walked away with wins far beyond what you would expect. Aside from luck, those people can also thank parlays (here's how they work in sports betting) for making it possible to win giant pots of money with minimal bets.

Parlay betting requires multiple bets on more than one outcome, with the more games involved lowering your odds of winning since you have to win every bet you've made to cash out. However, the more games you bet on, the more you stand to win. These "multis" or "accumulator" bets as they're called use a complex formula involving the fractional odds of each bet (first converted into decimals) being multiplied together before being multiplied again by the individual's bet. That number is then subtracted by the stake (e.g., $20), which gives the sportsbook your parlay odds.

This small parlay bet that paid out big happened in 2022 at NASCAR's Coke Zero Sugar 400 at Daytona. It was a near million-dollar payout on terrible odds, 74,087-to-1 to be exact. The bet was a $13.49 four-way parlay placed on FanDuel that required Cody Ware, B.J. McLeod, Landon Cassill, and David Ragan all finish in the top 10. A crash with only 23 laps to go helped the drivers finish higher than they may have otherwise. For instance, one driver hadn't made it past 17th place ever while another had never made it to the top 10 position in any racing cup before this one.

FanDuel would confirm it was the sportsbook's largest NASCAR race payout to date. When you consider that 20 out of 37 cars on the track that day ended up crashing and burning before making it to the finish line, you get a sense of the luck at play for the winner. If the odds of winning this bet weren't incredible enough, intense rain caused the race to be postponed and potentially not happen, as well as the fact that the $13.49 wager was made on a free bet. All of this makes the legendary small-bet win seem even more unlikely.

In 2021, a 12-leg parlay bet on the (delayed 2020) Ryder Cup needed for the following to happen: six favorites had to come out on top, four least-likely players had to win, and two more games had to end in ties. All 12 outcomes were called by a very lucky bettor who turned an $8 bet into nearly $1 million.

Another FanDuel winner, the psychic, time-traveling, or extremely lucky bettor somehow called major upsets, comebacks, and pretty specific final hole wins to make this win happen. The winner placed their bet in Illinois (which legalized sports betting in 2019).

Interesting to note, prior to America's victory in 2021, Europe had dominated the Ryder Cup the previous four meetings, which makes the winning parlays that much more risky. The major factors influencing the win were the selection of Jon Rahm, ranked first in the tournament, losing to the least-favored to win Scottie Scheffler (who happens to be No. 1 in the world in 2024). Also, the parlay correctly called two ties: Colin Morikawa versus Victor Hovland and Jordan Spieth versus Tommy Fleetwood.

This small-bet win is incredible not just for the amount of money wagered and won, but also the sheer unlikelihood of winning it. A successful 16-leg parlay bet on the winning teams of 10 baseball games, two NBA playoff games, and four NHL playoff games took this wager into the stratosphere. The year was again 2022, and the odds at 31,847 to 1, on a $6.90 ticket, led to a $219,746 win. The baseball games were nail-biters, by the way, as three of the games went into extra innings, and a fourth was decided by a single home run.

Caesars Sportsbook & Casino tweeted the unlikely parlay win, calling it epic. Part of that "epic" wager was that six out of the 16 bets were on underdogs. While there are a few ways casinos can trick you into spending money, this is obviously one time the house didn't win.

If you followed how much money people were betting on Super Bowl LVIII in 2024, you have a good sense of how popular betting on NFL games can be. For the 2023 season, a bettor picked 14 players to score touchdowns in week 16, and walked away with a cool $489,383 on a bet that set them back $5.

The bet was placed through DraftKings by Travis Dufner, who officially became ~$500,000 richer after San Francisco running back Christian McCaffery scored a touchdown during a Christmas Day game versus the Baltimore Ravens. This Christmas gift was celebrated by Dufner in his New Jersey home, with the moment he secured his win captured and shared for all by DraftKings on Twitter.

While it would be reasonable for a sportsbook to be less than enthusiastic about having to pay out nearly $500,00, DraftKings took it in stride. Of course, being one of the biggest online sports betting platforms in the U.S., which saw a 57% increase in revenue in 2023, it probably didn't exactly hurt its bottom line too much.

If you've ever wondered what it's like to win six figures on a small bet costing mere pennies, then look no further than this story. In 2022, a trio of betters in Pennsylvania correctly guessed which six players in six different NBA games would be the first to score a basket on the opposing team in a 50-cent bet.

The lucky winners should thank the athleticism of Lebron James, Christian Wood, Evan Fornier, Gordon Hayward, Bogdan Bogdanovitch, and Lauri Markkanen for netting them their win. Even the sportsbook that took the bet, FanDuel, tweeted disbelief: "THREE different customers in PA placed this first basket scorer parlay last night to turn $0.50 into over $130k," alongside a "mind blown" emoji.

The wager at 260,567-to-1 odds could've netted these three betters $26 million if they had bet a hundred dollars each. However, the return on investment on a 50-cent wager is nothing to be upset about, considering the $130,284 payout for each bettor. Speaking of which, there are a number of smart things you can do with just $10,000 to increase your overall net worth, nevermind $130,284. Hopefully, the small-bet winners sought out good financial advice for their winnings so they didn't end up like lottery winners who have ended up dead broke with nothing to show for it but regret.