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Biggest Upsets in Sports During 2019 – See the Best Underdog Stories

Mitch Robson

by Mitch Robson in News

Updated Dec 31, 2019 · 6:00 AM PST

Illinois football
Illinois football pulled off the biggest single game upset in 2019, by beating Wisconsin as 30-point underdogs. Photo from @SLGreenberg (Twitter)
  • 2019 saw major underdog stories across the sporting world from the St. Louis Blues’ Stanley Cup Win to the Stephen F. Austin upset of Duke at Cameron Indoor Stadium
  • The SBD team has rounded up some of the biggest upsets of the year and tracked their odds throughout their respective seasons
  • See all the best and biggest upsets of the past year below

If 2018 was the year of the dynasties as the Golden State Warriors, New England Patriots & Boston Red Sox won their respective titles, 2019 was the year of the underdog.

Long suffering fan bases with the Toronto Raptors, Washington Nationals & St. Louis Blues were finally rewarded with titles. Shane Lowry and Gary Woodland, two of the PGA Tour’s most well-liked journeymen, won themselves a major championship. Liverpool stormed back to win the Champions League after going down 3-0 in the first leg of an aggregate semifinal to Barcelona.

All of those championship underdogs along with numerous single game upsets led to an incredibly entertaining year of sports viewing and gambling. As 2019 wraps up, take a look back at some of the more notable underdog stories of the past year.

Notable Championship Underdogs of 2019

Team/Athlete Championship Won Longest Odds
St. Louis Blues Stanley Cup +6900 (January 28th)
Toronto Raptors NBA Championship +5900 (June 15th, 2018)
Washington Nationals World Series +5000 (June 16th)
Liverpool Champions League +8900 (November 8th, 2018)
Shane Lowry British Open +8000 (December 13th, 2018)
Anthony Ruiz Unified Heavyweight Title +1200 (May 28th)

Championship Droughts Broken in NHL, NBA & MLB

With Laura Branigan’s hit Gloria serving as the soundtrack to their miraculous Stanley Cup winning run, the Blues pulled off quite possibly the greatest underdog story of 2019.

After sitting in last place at the start of the 2019 calendar year and seeing their odds as high as +6900 on January 28th, the Blues fully bought into interim head coach Craig Berube’s message before storming through the playoffs and bringing the Cup back to St. Louis for the first time in four tries, and their first appearance in the NHL’s championship series in 49 years.

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Both the Toronto Raptors and Washington Nationals also captured the first championship in the history of each franchise after being big underdogs heading into the each of their respective seasons.

Just before the trade that saw the Raptors acquire Kawhi Leonard who was disgruntled in San Antonio, their NBA Championship odds sat at +5900, which would’ve presented incredible value had you read some tea leaves and seen that a possible Leonard trade to Canada’s only team was possible.

What followed was the perfect storybook season, as Toronto downed the dynasty in Golden State en route to their first championship in their first Finals appearance – and of course who could forget Leonard providing us with one of the most iconic shots we’ve ever seen.

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There had also been plenty of playoff heartbreak in the district over the years as the Washington Nationals built their contender from scratch after moving from Montreal.

After a stunning comeback victory in the NL Wild Card game, they stormed through the rest of the postseason on the backs of their two ace starters, Max Scherzer & Stephen Strasburg, to eventually defeat the heavily favored Houston Astros in the World Series.

The Nats had been as high as +5000 to win the World Series following their early season struggles, but stayed the course and rewarded their fans for sticking by them through all the trials of the past few years of disappointment.

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Big Men Get It Done on the Course & in the Ring

Shane Lowry became just the second ever player from the Republic of Ireland to win a major, joining Padraig Harrington, after being named Champion Golfer of the Year after winning the Open Championship at Royal Portrush in Northern Ireland.

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Lowry came into the week a +6700 underdog and had been as high as +8000 leading up to the tournament, before firing a 67-67-63-72 to run away with a six-stroke win at -15 to capture the title.

With the tournament also being the first major ever played in Northern – and Lowry being a native of the Republic of Ireland – he served as a unifying force and provided one of the most heartwarming sports stories of the year.

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Anthony Ruiz Jr. also pulled off an incredible stunner as a +1200 underdog against Anthony Joshua. Replacing Jarrell Miller who had failed drug tests in the fight for the unified heavyweight title, Ruiz Jr. scored a victory over arguably the best boxer on the planet by a 7th round TKO.

Notable Single Game Upsets of 2019

Game League Betting Result
Illinois Defeats Wisconsin 24-23 NCAAF ILL +29.5/+5000 ML
Evansville Defeats Kentucky 67-64 NCAAB EVANS +25.5/+650 ML
Stephen F. Austin Defeats Duke 85-83 NCAAB SFA +28/+9000 ML
Tigers Defeat Astros 2-1 MLB DET +450 ML
Dolphins Defeat Patriots 27-24 NFL MIA +17.5/+700 ML

College Basketball Blue Bloods Lose as Massive Favorites

With both teams experiencing major roster turnover coming into the current 2019-20 college hoops season, both Duke and Kentucky suffered stunning losses on their home floor in the opening weeks of the year.

On November 12th, former Wildcat player Walter McCarty took his Purple Aces into Rupp Arena and walked out with a 67-64 win over the #1 team in the country as 25.5 point underdogs.

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Just weeks later, Duke lost their first non-conference home game since 2000 to the Lumberjacks of Stephen F. Austin, who walked into Cameron Indoor Stadium and beat the Blue Devils in overtime.

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The 28-point spread and +9000 moneyline price on SFA presented the biggest college hoops upset in 15 years.

Tigers Pull Off Historic Win Against Verlander

Suffering through a long season of a rebuild in the Motor City, the Tigers had one shining light in August when they were able to take down their former ace.

Despite managing just two hits off Justin Verlander, Detroit squeaked out a 2-1 win as +450 underdogs – the biggest upset in Major League Baseball in 15 years.

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Make a Little Lovie Tonight

Lovie Smith has suffered through some trying years in Champaign as he was tasked with rebuilding the Fighting Illini football program, but this year his vision is starting to come together.

While reaching bowl eligibility for the first time in years after a comeback win against Michigan State, their biggest win of the season came in a stunning home upset of the Wisconsin Badgers in mid-October.

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As whopping 29.5 point home underdogs, they capitalized on Wisconsin turnovers and killed the Badgers playoffs hopes by winning on a walk-off field goal for the 24-23 win.

Dolphins Play America’s Heroes in Week 17

Ryan Fitzpatrick pulled out a little “FitzMagic” on the last Sunday of the decade, as the Miami Dolphins stunned New England in Foxborough to deny the Patriots a first round playoff bye since the 2009 season.

The ‘Phins came into the game as massive 17.5-point underdogs, but the defense tormented Tom Brady all afternoon including a pick six, and DeVante Parker was able to shred DPOY frontrunner Stephon Gilmore for over 100 yards receiving.

 

Which big upsets are you forecasting across the sporting world in 2020? Let us know in the comments below!

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