Most Creative Sports Betting Wins of the Week

Posted on December 17, 2020

You’ve got to love the creativity of sports bettors.

The new age has brought unprecedented flair and panache. From time to time, we highlight the Wager Wonderland of sports betting, as gamblers weave hunches, betting principles, and a sense of going against the grain to obtain colossal paydays.

Let’s take a look at the most creative sports bets of this week:

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While the news is exciting, we also present it to reveal strategy: why the bet won, what thought pattern was in play and where, if applicable, the gambler endured beads of sweat.

New Jersey claims its share of big tickets, but it doesn’t matter where the bets originated.

The gambling community celebrates its brethren, seeks future betting angles and asks:

“How did you come up with that?’”

Here’s a sample of the What and the Why of these most creative sports bets.

Moneyline Magic from DraftKings

Last week a  DraftKings bettor turned $50 into $39,016 by hitting a 12-team NFL moneyline parlay.

What makes the moneyline parlays great is that the player wisely avoided using the point spread.

Let’s examine the games and why that strategy worked.

The Moneylines:

  • TEN Titans -333
  • KC Chiefs -323
  • CHI Bears +105
  • ARI Cardinals -145
  • DEN Broncos +175
  • DAL Cowboys -159
  • TB Buccaneers -323
  • SEA Seahawks -1000
  • IND Colts -133
  • WAS Football Team +129
  • PHI Eagles +310
  • GB Packers -400

Game results:

The Titans beat the Jacksonville Jaguars, the Chiefs outlasted the Miami Dolphins, the Bears clobbered the Houston Texans, the Cardinals thumped the New York Giants, the Broncos upset the Carolina Panthers and the Cowboys humbled the Cincinnati Bengals.

In the second six, Tampa Bay outlasted the Minnesota Vikings, the Seahawks annihilated the New York Jets, the Colts outgunned the Las Vegas Raiders, Washington won on the road against the San Francisco 49ers, the Eagles upset the New Orleans Saints and the Packers beat back a feisty Detroit Lions team.

Why not selecting the spreads mattered

It was a beautiful ticket. Most of the teams covered outright, but the Packers were either a half-point loss or a push depending on when they were bet and the Chiefs, who defeated the Miami Dolphins by six points, would have been a loss. On a field goal in the final seconds.

The Genius

How about taking the Eagles outright to defeat the New Orleans Saints?  That pick alone should constitute a winning ticket here and in essence, it made the ticket. The Birds were the biggest underdog on the selection.

What a call, as the Eagles had lost four straight and the Saints had the biggest win streak in the NFC, nine games, coming in. This was gutsy because all the other successful picks would have been null and void without the Eagles, a one-touchdown underdog, upsetting the Saints


Road chalk was prominent last week and this ticket played right into that.

Picking Denver was a smart reach, because the game meant nothing to either team and how does one know who will show up?

Selecting Washington was a leap of faith for the NFC East and the selection was rewarded because Washington notched two defensive touchdowns, two more than its own offense, in a 23-15 road triumph over the San Francisco 49ers. Washington was +3.

After covering most of the ticket with road dogs, the bettor rolled the dice with the underdog Eagles.

Parlay Pandamonium at FanDuel

A FanDuel customer recently turned $17 into a payout of $3,757 on a 2-leg ML Parlay on college hoops picking the underdogs

  • Coppin State – Money Line +1600 (UNC Greensboro @ Coppin State). Coppin State prevailed as a big underdog, 86-80.
  • Portland – Money Line  +1200 (Portland @ Oregon State) Portland prevailed 87-85 in overtime. Imagine sweating that one out.

The beauty of this ticket is the idea of a reasonable amount of money placed on two teams.

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It underscores the uncertainty surrounding all sports, especially college basketball, early in the season.

It also shows that patrons don’t need a lot of money to make a big score.

Over-Unders… Another Way to Play

FanDuel other unique hits from the archives from November.

A customer placed $10 on a 13-leg parlay on NFL Total Points for a total payout of $44,221.

Nine of the selections involved the over, which has been the trend for NFL bettors throughout the year. There was one close call, with the Minnesota Vikings defeating the Green Bay Packers 28-22, with the over at 48.5

The call on the under 49 for the Kansas City Chiefs-New York Jets was revealing. The Chiefs were favored by 20 points, the highest total in the NFL this year. In taking the under, one is banking on dominance and for the underdog to be unable to score.  The bettor nailed it, with Kansas City’s 35-9 triumph featuring only 14 second-half points.

The same customer placed another $15 on another incredible 13-leg parlay on NFL Total Points for a total payout of $64,071.  The customer technically turned $25 into more than $100k.  

Yikes. $25 bucks into $100 K?

Who needs to work if you can do this?

Two more savvy strategies reported by FanDuel last month

A customer placed $5000 on the Buffalo Bills -4.5 against the New England Patriots. It was a loss because the Bills on by three, but the savvy bettor took the cash-out option while the Bills were up and made some money.

Great call. And the books love it too because they collect their vig on all the cash-out bets.

Here’s an example of going big on one game. FanDuel Sportsbooks biggest payout in that same week was a $500, 11-leg bet that paid $13,153.

All Kansas City Chiefs, all the time against the New York Jets.

Patrick Mahomes Over 277.5 Passing Yards
Tyreek Hill Over 64.5 Receiving Yards
Travis Kelce Over 63.5 Receiving Yards

  • Chiefs First Half Money Line
  • Chiefs Second Half Money Line
  • Chiefs -4.5 1st Quarter Spread
  • Over 10.5 Total Points 1st Quarter
  • Chiefs Money Line  Chiefs -10.5
  • First Half Spread Chiefs 1st Quarter Money Line
  • Chiefs Second Quarter Money Line

This speaks to the wisdom of seeing a game a certain way, anticipating every nuance and slamming it.

Free is ME…and worth over 3K

It pays to compile free bets.

That may not be more evident than in a midseason hit reported by DraftKings Sportsbook. A customer turned a $50 free bet into more than $3,000 by hitting a five-team moneyline wager.

This bettor took the Miami Dolphins over the Los Angeles Rams, the Pittsburgh Steelers upset over the Baltimore Ravens, the Denver Broncos over the Los Angeles Chargers, the Seattle Seahawks over the San Francisco 49ers and the Las Vegas Raiders over the Cleveland Browns.

There are millions of dollars pouring through the nj online sportsbooks each week. It is safe to assume that many of these multi-leg parlays have companion tickets, in which the same handful of teams appear on both tickets.

In a 12-team ticket, for example, if your six “anchor” teams hit, you can change the teams on the other six, thereby guaranteeing that six correct picks turn into a 12-teamer.

Good luck betting and we’ll periodically check back with Wager Wonderland.

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.

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