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OddsChecker Wrapped: Our Handicappers' Best and Worst Bets of 2021

In order to celebrate the New Year, we take a look at some of the best, and worst, bets from our top handicappers in 2021. With OddsChecker Wrapped, you have the chance to win a $250 sports gift card by sharing your best or worst bet of 2021.
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OddsChecker Wrapped: Our Handicappers' Best and Worst Bets of 2021

2021 is officially coming to a close!

We've all had our share of great bets this past year, and we've also had our share of head-scratchers. So, as a way to celebrate, we're giving you the chance to win a $250 gift card by participating in OddsChecker wrapped.

Right now, you can share your best or worst bet from this past year by replying to the tweet below with a screenshot. If we think you have the best, or worst, bet from 2021, you win a $250 gift card!

But, it wouldn't be fair if we only asked you guys to share your best and worst plays of 2021. So, we asked some of our top handicappers to share with us some of their highest of highs and lowest of lows from this past year.

So, let's take a look at the best and worst bets from our handicappers in 2021!

OddsChecker's Best and Worst Bets of 2021

Geoff Fienberg

Best Bet of 2021: Tony Finau to win Northern Trust (+6600)

When you finish 2021 with as many winners as Geoff, it's tough to pick just one as your favorite. We would have thought it was his Viktor Hovland special that he hit. But, Geoff's favorite (and best) bet of the year comes to us with his Finau winner at the Northern Trust. Finau had let so many bettors down for so long that the bookmakers decided to post an insane +6600 on him, and Geoff pounced.

Worst Bet of 2021: Colin Morikawa to miss the cut at The Open (+350)

You need to take the bad with the good, and this one was Geoff's worst bet of 2021. Not only did Morikawa not miss the cut, he went on to win the event by shooting 15-under par. There's no shame in taking a risk, especially in golf betting, but this is one that Geoff definitely wants back.

John Hyslop

Best Bet of 2021: Alabama TTO 20.5 vs. UGA (-110)

It's tough to pick John's best bet of 2021 because, as you're well aware, his bets have a 0% chance of losing. Remember, win probability shifts as the game moves on, but when he makes his bets they are all sure winners. If you have a problem with that, your issue is with math, not John. This specific bet for the SEC title game was a truly sharp one. Georgia went in having not given up more than 17 points all season and sporting the best defense in the country. Bama came out and hung 41 points on the Dawgs. This one was never in doubt.

Worst Bet of 2021: Frank Darby Over 5.5 Receiving Yards (-110)

This bet came to us on October 10 as the Falcons took on the Jets in London. 9:30 AM kicks can make a man do funny things, like betting on Frank Darby to finish with more than five yards. In John's defense, the Falcons were shorthanded at WR and Darby getting a few targets didn't seem unrealistic at the time. But, Darby has one catch for 14 yards on the year so far, and it definitely didn't come in this game.

Matt McCuen

Best Bet of 2021: 5-Leg SGP for Bills vs. Saints (+3000)

Who can forget this one from the man DeadPresPicks? With the entire sports betting world looking for a winner to close out Thanksgiving night, our guy Matt came through with an absolute bomb at +3000. This same game parlay had it all. Rushing yard props, anytime TD scorers, receiving yard props and a play on the game. In the end, we all came out on top after tailing Matt here.

Take a look back on Matt's Thanksgiving night Same Game Parlay winner

Worst Bet of 2021: St. Bonaventure ML vs. Virginia Tech

Even sharps like Matt can get humbled by sports betting every once in a while. At the time, it seemed like a good play, taking a solid St. Bonaventure team to defeat Virginia Tech earlier this month. But, in the end, it was a 37-point loss by the Bonnies that made this one a loser from the start. Looking for a positive? At least we didn't have to sweat this one out.

Josh Gayle

Best Bet of 2021: LeBron James Over 5.5 3Q Points (-135)

Josh, also known as ThatGuyBets on Twitter, described this one as his favorite cash ever! Recently, Josh had made 3Q NBA bets his niche market, so much so that DraftKings has even removed the market. This one holds a special place in Josh's heart because it took 56 seconds to hit at LeBron opened up the 3Q with back-to-back three-pointers to make this one a winner.

Worst Bet of 2021: Jayson Tatum Top Point Scorer (+105)

This Tatum one is a heartbreaker. DraftKings made a mistake leaving up Tatum as leading scorer at + odds after Giannis, Middleton and Jaylen Brown were all out of this one. Tatum's projected PTS were 10 above the next highest player and Josh thought he had a sure thing. The one player he said he feared was Jrue Holiday with no Middleton/Giannis, but he wasn't the man who stopped this winner. Tatum had a respectable 27 points but it was no match for Dennis Schroeder putting up 38. Josh remembers watching that game and screaming at him to pass but he had no interest.

Gray Gutfreund

Best Bet of 2021: Bogdan Bogdanovic o18.5 Points + o3.5 Threes Made (+179)

Just by looking at the tweet below, you can see the research that went into this one hitting. It makes it that much sweeter when it hits at +179 odds as well. Gray has found a niche as a prop bet guru and has spent the entire year churning out winner after winner. This Bogdan Bogdanovic was another truly sharp play from Gray that ended up cashing and making money for anyone that tailed

Worst Bet of 2021: Allen Robinson o5.5 Catches (-133)

It happens to the best of us. We do all the research, get hyped up for a pick and then the player comes out and lays an egg. That's exactly what happened here. Robinson to go over 5 catches sat at -133 and he didn't get close. He finished this came against the Bengals with 2 catches for 24 yards.


Here at oddschecker, we have a team of highly-experienced writers, who keep their finger on the pulse when it comes to the latest sports and betting news and predictions. This gives us the ability to bring you all the information you need when it comes to your favorite sports.


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