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The Surest Bets and Biggest Upsets in Sports History

Nick DimengoOct 6, 2014

I don't know about you, but for me, one of the best parts about sports is the unpredictability that it gives fans.

Just when we think that we know something, boom—the complete opposite happens, leaving us wondering if we're as knowledgeable as we claim we are.

Since we love being right—but also love when something shocking happens—I figured I would put together a list of some of the surest bets and biggest upsets we've seen in sports recently.

I hope you were on the winning end of some of these outcomes.

Sure Bet: Peyton Manning vs. Tom Brady

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The two greatest signal-callers of the past 15 years, Tom Brady and Peyton Manning share a few things in common.

They both have won multiple league MVPs. They both own Super Bowl rings. They both will have a bust in Canton one day. And they both play each other nearly every single football season since 2001.

It's no joke—check the facts!

We all know that these two will always draw a crowd, so, while it might be difficult to guess who's going to win between the two, fans can probably bet on seeing them square off every season until one of them calls it quits.

Upset: Super Bowl Rematches

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There is typically no reason why a Week 3 matchup between NFL teams should draw a lot of attention, yet that was the case a couple of weeks ago when the Seattle Seahawks hosted the Denver Broncos.

What was all the fuss about?

Well, as we all probably recall, Seattle and Denver faced off in last season's Super Bowl, making it just the sixth time that the two teams who played against each other in the Super Bowl matched up in the following regular season.

In fact, since February when they met in the big game, the teams have played three times—including a preseason matchup in August—meaning that this could silently become one of the newer NFL rivalries.

Unfortunately for the Broncos, the only game they won was the meaningless preseason affair.

Sure Bet: L.A. Kings or Chicago Blackhawks Win Stanley Cup

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In case you haven't paid attention, four of the past five NHL seasons have ended with either the Chicago Blackhawks or Los Angeles Kings lifting the Stanley Cup, with the Kings set to defend their crown as the puck drops again this month.

That's not necessarily a sure thing, but as someone who likes to gamble, I'd take the odds to go with them—especially now that the Hawks have secured young stars Jonathan Toews and Patrick Kane.

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Upset: Dallas Mavericks Winning 2011 NBA Title

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This may not have been one of the biggest title-shockers ever, but when it comes to the NBA Finals, one can't help but think that it ranks up there.

Everything was working against the Dallas Mavericks when going head-to-head against the Miami Heat in the 2011 NBA Finals.

The Heat—in their first season with three future Hall of Famers—were the people's and experts' pick to win it all.

That is, until Dirk Nowitzki showed why he was a former league MVP and future Hall of Famer himself, and LeBron James suddenly forgot what it was like to play as the best player in the world—especially when it mattered most.

Sure Bet: No. 12 Seed Beats a No. 5 Seed in NCAA Hoops Tourney

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Want to win your bracket? Make sure you choose a No. 12 seed to defeat a No. 5 seed on the first couple of full days of games.

While the rest of your bracket will totally be busted by the end of the first weekend, you can take solace in knowing that you (hopefully) chose the correct upset, seeing how this has occurred in 27 of the past 30 NCAA tournaments, with three No. 12s winning in 2014.

Filling out your bracket can become an obsessive, back-and-forth science—but it shouldn't be when matching up these two seeds.

Upset: The NCAA Forming a Playoff System

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OK, so this was bound to happen at some point in our lives, right?

There's actually no need to answer that any longer, because the NCAA finally got something right and booted the BCS to create what every sport has to decide a champion—a damn playoff system.

While it still incorporates some subjectivity from a committee to decide who the top four teams are—meaning it's bound to have some arguments—it's a hell of an alternative to the process it just replaced.

Sure Bet: Clayton Kershaw Finishes in the Top 3 for Cy Young Voting

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He may not always win it—though, if you want another safe bet, he probably will this year—but L.A. Dodgers ace Clayton Kershaw will undoubtedly finish in the top three of voting for the Cy Young Award each season he plays.

Still just 26 years old, the lefty is, generally speaking, still in the early stages of his prime, yet he has finished in the top three in Cy Young voting the past three years, winning twice, with his third Cy Young bound to happen at the conclusion of the postseason.

Kershaw is the best pitcher in the game, and until he shows otherwise, there's no reason to bet against him racking up the individual awards.

Sure Bet: Mike Trout Wins AL MVP

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Much like Clayton Kershaw winning the Cy Young Award this season is a near forgone conclusion, many believe that L.A. Angels outfielder Mike Trout will finally earn his first league MVP.

No, it's not like Trout has been searching for one over a long career—he's still just 23 years old and in his third full season—but because he has finished as runner-up in voting to Miguel Cabrera the last two years, it's probably a small monkey lifted off of his back.

Trout can do it all and is widely considered the best position player in the game, so, while this is technically an upset in the sense that he won't just be sitting in second, it's probably just the first of many for the guy.

Sure Bet: Mount Union and Wisconsin-Whitewater in D-III Title Game

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One might be hard-pressed to find diehard Division III college football fans.

But for those who follow the lower-level schools that aren't televised nationally—or, sometimes, even locally—they are well aware of the rivalry that's been going on between Mount Union and Wisconsin-Whitewater, as the teams have faced each other in seven of the past eight title games.

Even if you've never expressed any interest in D-III sports, it's a safe bet to assume these two will somehow, some way, meet in the playoffs.

Upset: The SEC Didn't Win the National Title

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While the aforementioned D-III national title is fairly easy to predict—if that's possible in sports—the big boys in D-I have suddenly found themselves with a few more teams that might be capable of winning a championship.

That's because, after a seven-year run of cradling the crystal football at season's end, the SEC's reign of winning a national championship ended in 2013.

With defending champ Florida State from the ACC—and currently ranked No. 1 in the country in both major polls, per ESPN.com—knocking off the Auburn Tigers last year, and the inclusion of the College Football Playoff this season, saying an SEC team will win might still be very smart, but it isn't as simple as it was the past seven years.

The SEC is still head and shoulders above the rest of the conferences in the nation, but the gap may have closed because of the few aforementioned factors.

Sure Bet: Floyd Mayweather Jr. Will Win

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Whether you're a Floyd Mayweather Jr. supporter or not, fans need to at least respect the guy for being the best at his sport.

Even at 38 years old, the boxer is still a perfect 47-0 in his career, meaning that he has never tasted what it's like to walk out of the ring bloodied without a belt.

That's pretty damn impressive, meaning any time he steps between the ropes, there's absolutely no reason to say anything other than, "He's going to win," considering that's all he does.

It's no wonder the guy is as cocky as they come.

Upset: Manny Pacquiao Will Fight Floyd Mayweather

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While the safest bet in sports might be predicting the outcome of a Floyd Mayweather Jr. fight, one of the sketchiest is guessing when—or if—he'll ever step onto the canvas against Manny Pacquiao.

Hands down the two greatest boxers of this generation, getting these two together would create a buzz like Mike Tyson and Evander Holyfield did in the late '90s or Kobe Bryant and LeBron James would do in an NBA Finals matchup.

There has been chatter about a fight being scheduled for years, so let's all hope that the latest buzz, via James Patrick Quizon of IBTimes.com, actually brings it to fruition.

Sure Bet: Super Bowl Prop Bets

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Want to know how to make some serious money doing Super Bowl prop bets? Talk to Jona Rechnitz, who has happened to do it twice in the past three years.

First winning $50,000 by picking a safety would happen in the 2012 Super Bowl between the New England Patriots and New York Giants, Rechnitz figured he would try his luck on the same bet in last year's big game.

And wouldn't you know it, the guy actually won it again, this time collecting $25,000 for choosing the safety that happened on the first play of the game when an errant snap sailed over Peyton Manning's head for a safety.

Sometimes it really is better to be lucky than good.

Upset: Picking All 15 NFL Games Correctly

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For those who have ever tried their hand at gambling, you know how difficult—and frustrating—it is to choose the correct winners.

There's honestly no telling what's going to happen or what twists a contest will take, with teams that are favored by double-digits points somehow—inexcusably losing—ruining your chance at winning money.

But for some, that's not the case, as a few guys have correctly chosen the winners to all 15 games in an NFL weekend.

Most recently was an Arizona man who simply goes by Rex, who just two weeks ago won $57,000 after the Chicago Bears beat the New York Jets on Monday Night Football.

I don't care who Rex's favorite team happens to be, I give him a free pass to become a bandwagon Bears fan if he so chooses—unless this is a conspiracy and it's really Jets head coach Rex Ryan.

Sure Bet: San Antonio Spurs Win 50-Plus Games and Make Playoffs

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Want to know what it takes to build a consistent contender? Look no further than those damn San Antonio Spurs.

While other franchises look for quick fixes when a season goes awry and recycle coaches and front-office leaders without batting an eye, the Spurs just go about their business as usual.

Not only have they made the playoffs in each season since drafting future Hall of Famer Tim Duncan first overall back in 1997, but after going 62-20 and winning another NBA title this past season, they've now had 15 straight years of winning 50-plus games.

Maybe more impressive is that they aren't just sneaking in; rather, they've remained in the upper echelon of Western Conference teams—never finishing less than the No. 2 seed since drafting Duncan. So, yeah, permanent-marker them into the playoffs until further notice.

Upset: LeBron James Returns to Cleveland Cavs

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With those three words in his Sports Illustrated piece, LeBron James, Akron's prodigal son, turned the NBA landscape upside down and shocked the basketball world.

Rather than attempt a fifth straight NBA Finals appearance with his buddies Dwyane Wade and Chris Bosh down in South Beach, Bron chose home because of his heart, returning to the gray skies of Cleveland instead of the sunny ones in Miami.

Sure, there was always a possibility and, as a born-and-bred Clevelander, a wishful hope that he would return, but not while still in his prime.

It wasn't until after he opted out of his contract following the Heat's loss to the aforementioned San Antonio Spurs that buzz really started about a return to Ohio for James.

Seeing him actually do it would have never been guessed just a month prior to his announcement.

Sure Bet: San Francisco Giants Win 2014 World Series

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Going a combined 162-162 in 2011 and 2013, the Giants seem to always save their best for the even-numbered year since 2010.

No, seriously, they have won two World Series titles—2010, 2012—and find themselves in the postseason once again this year, winning Game 1 of their Nation League Division Series showdown with the Washington Nationals.

Now, I'm not quite ready to say go all-in on the Giants, but if history really does have a way of repeating itself and you're a believer in trends, than I'd go ahead and happily toss a few extra bucks at having them celebrate with champagne in their clubhouse at season's end.

Upset: Kansas City Royals Make Playoffs

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As has been the case a few seasons in the past, the 2014 Kansas City Royals were expected to be better than they traditionally have been.

But like years past, many believed that the Royals would fall short of expectations and put together anything but a K.C. masterpiece of a season.

Well, this isn't your older siblings' Royals, instead mirroring that of your parents when they were still in their heyday.

That's because these Royals finally ended a 29-year postseason drought, winning the American League Wild Card—and AL Wild Card Game—to give their fans something to cheer about for the first time in nearly three decades.

It was always a possibility, but I would have bet you there weren't too many who actually would have put money down on the Royals to do anything more than maybe finish above .500.

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