Top 10 biggest betting upsets of 2021

Oral Roberts Golden Eagles celebrate their 81-78 victory over the Florida Gators during the second round of the 2021 NCAA Tournament on Sunday, March 21, 2021, at Indiana Farmers Coliseum in Indianapolis.
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Andrew Ortenberg

NFL· 4 weeks ago

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I'm an editor here at Pickswise who was raised in a household full of sports fanatics. Since I unfortunately never had LeBron James' jumping ability I wasn't able to make it to the NBA, and chose writing about sports as the next best thing. An avid sports bettor myself, I'm excited to get to write about the industry as it gets set to take off across the country. Buckle up.

The year 2021 has been truly unlike any other, and now it’s coming to an end. As we get ready for the New Year, it’s time to take a look back and reflect. This year was a return to relative normalcy for sports bettors, as we got back a bunch of awesome events (like March Madness) that we didn’t have in 2020 due to COVID.

There was a lot to be thankful for this year. The sports gambling landscape continued to evolve, with plenty of new states legalizing betting and more to come in 2022. This year was a rollercoaster with plenty of highs and lows, but one constant was that there were tons of upsets. Many massive underdogs emerged victorious, which for many was a bettor’s paradise, but for others (especially those who fancy heavy-favorite Money Line parlays) a nightmare. With that in mind, here’s a Pickswise countdown of the 10 biggest upsets from the year in sports betting:

10) NFL: December 19th – Lions (+500 ML) stun Cardinals

This one got in just before the bell, happening only a couple of weeks ago. The fighting Dan Campbells (+500 ML) shocked Kyler Murray and the Cardinals, as the scrappy 1-11-1 Detroit team pulled off the second-biggest upset of the NFL season. Plenty of people were lining up to lay 13 points with Arizona, who ultimately lost outright while getting carved up by Jared Goff. And they didn’t just lose; they got dominated. Any given Sunday, as they say.

9) NCAAB: March 20th – Abilene Christian sinks Texas in March Madness

Upsets and March Madness go together like eggs and bacon. You truly can’t have one without the other. After missing the entire tournament the year before due to the pandemic, this one was extra special, and the on-court action certainly didn’t disappoint. 3-seed Texas was a trendy Final Four pick (including by myself) but lost outright to 14-seed Abilene Christian (+340 ML) in the first round. So it goes.

8) MLB: Braves (100/1) make miracle World Series run

Unlike the rest of this list, this one isn’t about a single-game upset. Rather, it was a miraculous run that included plenty of upsets along the way. But we couldn’t talk about underdog stories from 2021 without mentioning the Braves. Atlanta started slow, and they were below .500 at the All-Star break. Around that time, you could’ve got them as high as 100/1 (!!!) to win the World Series. They turned things around in the second half, and started a memorable journey to the playoffs. Then they finally slayed the dragon and upset the Dodgers in the NLCS to advance to the Fall Classic, where they bested the Astros as underdogs yet again.

7) NCAAF: October 16th – UL Monroe (+4000 ML) tops Liberty with epic third quarter

Upsets are almost as synonymous with college football as they are with March Madness. And we had some big ones this season. It wasn’t the most high-profile game, but what UL Monroe (+4000 ML) did to Liberty was close to incredible could arguably be closer to the top spot on this list. The Warhawks have often been regarded as one of the worst teams in the FBS, and even went 0-10 in last year. As such, they found themselves as +32.5 underdogs to Liberty on October 16th. They shocked everybody by outscoring the Flames 28-0 in the third quarter en route to a 31-28 victory.

6) Soccer: September 28th – Sheriff Tiraspol (+2000 ML) topple Real Madrid

Turning our attention to the soccer pitch, nobody gave Sheriff Tiraspol much of a chance when they had to take on European giants Real Madrid in September. As whopping +2000 Money Line underdogs to win the match, they pulled off one of the biggest upsets in Champions League history, earning a 2-1 win thanks to a thrilling last-minute goal. It was a true David vs Goliath moment with one of the titans of the sport toppling in shocking fashion.

5) Tennis: July 26th – Marketa Vondrousova stuns Naomi Osaka at Tokyo Olympics

Naomi Osaka wasn’t even supposed to break much of a sweat during her match against Marketa Vondrousova in the third round of the Tokyo Olympics. Osaka was one of the faces of the Olympics, lit the Olympic cauldron that opened the games and was a -650 favorite on the Money Line for this match. She stunningly lost in straight sets, 6-1 and 6-4. And not too long after, Osaka was upset as an equally large favorite by Leylah Fernandez in the U.S. Open in September, after which she announced her intention to take a break from professional tennis.

4) NFL: November 7th – Jaguars (+750 ML) shock the Bills

The Urban Meyer era in Jacksonville was mostly a disaster, filled with seemingly endless lows. But his short tenure did have one high point. The biggest upset of the 2021 NFL season, when the Jaguars beat the Bills as underdogs of 16 points. It wasn’t exactly the prettiest win, as Jacksonville won an ugly 9-6 defensive struggle, but it was a moment that rocked the NFL landscape. It was the first game that had many questioning whether or not Buffalo was a legit title contender, and it started to expose some of their flaws. Meyer is back checking the classifieds section now, but he’ll always have this game.

3) UFC: December 11th – Julianna Pena (+700) submits Amanda Nunes

This one also just happened in the final month of the year, and nobody saw it coming at UFC 269. Amanda Nunes was on top of the fighting world and was installed as a huge -1200 favorite for this bout with Julianna Pena. One unlucky bettor even lost $318K banking on Nunes to keep up her dominance. At +700 on the Money Line, Pena’s victory was one of the biggest shockers in UFC history. In fact, Joe Rogan proclaimed after, “That’s the biggest upset in the history of this sport!” Fortunately for MMA fans, Nunes announced soon after her loss by submission that she wanted a rematch, so we may get a Round 2 here. Maybe we’ll see this matchup again in the 2022 version of this list…

2) NCAAF: November 13th – Kansas (+2800 ML) beats Texas 57-56 in shootout thriller

Kansas doesn’t beat Texas. It’s just not something that happens. Except in 2021, that is. The Jayhawks have been a doormat in the Big 12 for over a decade and are routinely regarded as one of the worst Power 5 teams out there. Nobody told them that before their game against Texas, though. Entering as 31-point underdogs, Kansas (+2800 ML) pulled off a 57-56 win in one of the most thrilling games of the season. The shootout went to overtime, and in OT Kansas elected to go for the kill with a two-point conversion attempt for the win. You have to respect the guts from a team that hasn’t had too many moments of glory in recent years. It was a humiliating loss for the Longhorns and a stark reminder that they’re a long ways away from their former status as a top program.

1) NCAAB: Oral Roberts – the March Madness Cinderella of 2021

The true Cinderella team of this year was Oral Roberts. The Golden Eagles set the tone for a wild March Madness, beating 2-seed Ohio State as 16-point underdogs and as high as +1200 on the Money Line in one of the first games of the tournament. But they deserve the top spot here because they didn’t just do it once, but twice. Against all odds (specifically +340 ML this time), the Golden Eagles went on to shock Florida in the Round of 32 to advance to the Sweet 16. And they almost did it again in the Sweet 16, losing by 2 against Arkansas to miss out on a trip to the Elite 8. As someone who was on the ORU Money Line in that first game against Ohio State, I can’t thank Max Abmas and the Golden Eagles enough.

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