Wager Wonderland: Sports Bettors Who Defied Impossible Odds With 6-Figure Wins

Posted on December 4, 2019

Cha-cha-cha ching!

Hear those bells and whistles? Sound the sirens. Start the music.

Like country club members, gamblers are united by the pursuit of the big score and curious about what’s possible.

Who saw that? The bettor did what? When will I win that much?

For several sports bettors, the when just happened.

New Players get up to $150 in Bonus Bets at FanDuel Sportsbook
Bet $5
Get $150
If Your Bet Wins
Bet $5 Get $150 in Bonus Bets if Your Bet Wins
Available on Desktop, Android & iOS
To Claim: Click Play Now

$229,000 win on ONE TICKET

It’s a Wager Wonderland fiesta as FanDuel confirmed a phenomenal payout of nearly a quarter-million dollars on one sports betting parlay ticket from late November.

A moneyline bet of $200 on 15 teams became $229,276.50 in one magical flash.


The FanDuel phenomenon springs from a wager placed Nov. 25.

A 15-team moneyline parlay across the NFL, NBA and NHL.

The victory wasn’t official until the end of NFL Week 13 and not confirmed until early in the week.

This moneyline belongs on a slot machine, with correct sports betting parlay selections lined up like a sea of 777s. There is no such thing as a 15-team easy parlay hit, but this ticket combined the right mix of strategy and breaks.

The winning strategy?

sports betting parlay winners

So, how did he do it? Start with prohibitive moneyline favorites and try to squirm through the tight games.

Bing, bing, bing came the NBA deluge of wins.

Wins were made by the Brooklyn Nets, Indiana Pacers, Detroit Pistons, Miami Heat, Minnesota Timberwolves, Toronto Raptors, Boston Celtics, Portland Trail Blazers and Milwaukee Bucks.

Most were considerable favorites, although the Nets were -102 and gained a 2-point road win against the Cleveland Cavaliers.

Think that was close?

How about a 1-point, nail-biter with the heavily favored Celtics squirming past the Sacramento Kings, 103-102?

In two other tough games:

  • The Raptors edged a game Philadelphia 76ers squad by 5 points.
  • And the Bucks survived a 4-point verdict against the Utah Jazz.

All of these bets hinged on a bucket or two.

The NHL was nothing but sweat, as the Columbus Blue Jackets, New York Rangers and Philadelphia Flyers all won by one goal, and the Rangers needed overtime.

The strategy, which included a Dallas Stars selection, involved picking all home teams.

One final matchup … to win $229,276

What would $229,276.50 be without a drum roll?

The $229,000+ win came down to one game: Baltimore Ravens versus San Francisco 49ers.

Hard to be more dramatic than Baltimore’s kicker, Justin Tucker, drilling a game-winning, 49-yard field goal in the rain.

The Baltimore moneyline pick was good!

Baltimore edged out the Niners 20-17 in the league’s marquee matchup.

Think about the teams lining up for a field goal worth nearly a quarter of a million dollars, realizing you may never be in this position again and watching it float through the uprights.

Anxiety and euphoria were on one life-changing boot.

Turning $500 into $14,249

On Monday night, a customer turned $500 into $14,249 with a three-leg sports betting parlay ticket on the Minnesota Vikings-Seattle Seahawks tilt.

  • Seattle’s 37-30 triumph easily covered the over 48.5 and Seattle moneyline.
  • The touchdown by Davin Cook, at +580, made the payout.

Happy Thanksgiving at PlaySugarHouse

Sports bettor’s favorite Turkey Day greens have nothing to do with vegetables.

Logic and conviction created digital greenbacks and a holiday feast for this PlaySugarHouse customer willing to commit $500.

The bold wager returned $16,416, odds of better than 30-1 on a Thanksgiving sweep.

The patron took:

  • The Saints at -6.5 versus the Falcons and the under of 48.
  • The Buffalo Bills on the moneyline as an underdog versus the Dallas Cowboys.
  • And the Chicago Bears moneyline versus the Detroit Lions.

Ironically, the only game in which this bettor cruised was with the underdog, Buffalo, which crushed Dallas 26-15.

Chicago had to overcome a 10-point road deficit, score late and hold off a deep Detroit drive in the final seconds.

And before the Saints toppled the Falcons 26-18, the bettor had to absorb a Ground Hog Day nightmare with Atlanta converting an unprecedented three consecutive onside kicks. One was called back for a penalty.

When $16,416 is in sight, the end of the clinching game never moves fast enough.

Get Up to $250 Bonus at BetRivers Sportsbook
$250 Bonus
2nd Chance Bet
Up To $250 in Bet Credits
ONLY 1x Play Through!
Use Affiliate Code: PLAYRIV

Rags to riches?

Money Monday Club

Another PlaySugarHouse gambler was living right with a $5 stab that returned a hefty $3,354.14.

A $5 bet won him $3,354.14!

How, you ask? Here’s how:

  1. This ticket was five games and 10 bets.
  2. Each game required two correct selections.

This one featured the Tennessee Titans beating the Indianapolis Colts and the game hitting more than 43.5 points.

  • A blocked field goal that went for a Tennessee touchdown made that bet win.

How about the Green Bay Packers to beat the New York Giants and the over 43-point total?

  • The final of 31-13 Green Bay was just enough.

Pittsburgh defeating Cleveland 20-13 came in under the 39 limit.

Remember the New York Jets scoring more than 30 points three weeks in a row? And, then facing the winless Cincinnati Bengals? Ha!

  • This bettor took a misdirection, with the winless Bengals to win and the under 43.5 total.

That was genius, as Cincinnati won 22-6.

To cap it off, the bettor took the Washington Redskins at +10 versus the Carolina Panthers, and the over of 39.5 total points.

The Redskins won outright 29-21 after trailing 14-0.

PointsBet: The dog ate my parlay

Remember the old excuse about the dog eating your homework? Well, the heavy underdog Miami Dolphins and Washington Redskins destroyed an apparently logical moneyline parlay bet played at $35,000.

The bet would have returned roughly $14,000 and one can understand the strategy:

Take two guarantees, don’t worry about the spread, just win the games and take a small profit.

We’ve seen this approach work with big-money leverage creating payouts in the thousands. But when NFL odds dogs bite, they can demolish a bankroll.

Get up to $1,000 in Second Chance Bets at Pointsbet Sportsbook
Get Up to $1,000
In Second Chance Bets
Get up to $1,000 in Second Chance Bets
10 Bonus Bets up to $100 each
To Claim: Click Play Now

And when they don’t, big money can capitalize. PointsBet’s standard wagering realm yielded a $33,000 payout on the Kansas City Chiefs to cover 11 points against the Oakland Raiders.

The Chiefs romped 40-9.

In the PointsBet realm, in which every yardage and touchdown total is magnified, heavy favorites delivered wads of cash.

How about the Los Angeles Rams winning 34-7 against the Arizona Cardinals at $500 a point?

The Rams were giving 3.5 and won by 27, thus bringing home 23.5 times the $500 …

or $11,750!

Going to top-ranked college football powerhouse LSU also became lucrative.

One player took a $500-a-point ride on LSU, which triumphed 50-7 over Texas A&M.

LSU won by 43 points, 25.5 over the 17.5 spread.

Thus, securing a cool $12,750.


ny giants eli manning

Legalized sports betting, with deep-pocket operators, have shattered projections originally given by gambling proponents.

Why? Call it trust.

Unlike previous forms of illegal wagering, gamblers don’t worry about collecting their winnings. Imagine tossing a $200 pie-in-the-sky sports betting parlay ticket at illegal operators in the pre-legal sports betting era.

One would not believe a bet of this size would be paid.

The books are dependable banks and creative enterprises. No one could have foreseen the magnitude of five-figure bets placed into the system by gamblers grateful to have restrictions lifted.

The Whales have been unleashed.

Claim Your $1,200 Bonus at DraftKings Sportsbook
Up to $1,200 BONUS
New User Bonus. T&Cs Apply
Bet $5 Get $150 in Bonus Bets
PLUS up to $1,000 Deposit Bonus
PLUS $50 Bonus Bet on Deposit
PLUS No Sweat NBA SGP Every Day of Playoffs
Gambling Problem? Call 1-800-GAMBLER 
Dave Bontempo Avatar
Written by
Dave Bontempo

Dave Bontempo, a national multi-award-winning writer, and broadcaster, writes extensively on the evolving legalized sports-wagering world. Over the past four decades, he has called fights for all major networks, authored columns for the Associated Press, Atlantic City Press, and iGaming Player. He is in the New Jersey Boxing Hall of Fame, the Atlantic City Boxing Hall of Fame and a Sam Taub Award for broadcast excellence, given by the Boxing Writers Association of America.

View all posts by Dave Bontempo
Privacy Policy