The Greatest March Madness Underdog Picks — Top 9 Cinderella Stories

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Championships are nice when you’re rooting for your favorite team, but March Madness is more than just a race to the win. The tournament is filled with suspense, excitement, and heartbreaks as we witness upsets and bracket busting in real time.

A good underdog versus superstar show is to March Madness what a mind-blowing plot twist is to cinema. Underdogs blowing brackets sometimes go down in NCAA history. In preparation for 2023’s tournament, we went back in history through top seeds, upsets, blowouts, and of course Cinderella stories to compile a list of the 9 greatest March Madness underdog stories.

Let’s see what made these teams stand out.

Why Are March Madness Underdogs Such a Big Thing?

Sports fans seem to have a soft spot for March Madness, and rightly so. The NCAA Division I men’s basketball tournament is one of the most anticipated events. With 68 teams battling for the winner title, the tournament has kept viewers glued to their seats since 1939. 

With so many players competing in seven rounds for the national championship, you can expect different matchups to spice up the game. To make matters even more intense, March Madness’ bracket system can lead to impressive upsets. 

The tournament is packed and the first four days are all intense, exciting matches filled with action, suspense, and heartbreak. 

Event	2023 Date
Selection Sunday	Sunday, March 12
First Four	March 14-15
First Round	March 16-17
Second Round	March 18-19
Sweet 16	March 23-24
Elite Eight	March 25-26
Final Four	April 1
NCAA Championship Game	April 3

With so many factors to take in, you’d normally expect every other season to have some sort of surprise. We’ve already seen a huge surprise this year, when Texas Southern and Kennesaw State made the NCAA Tournament cut, but North Carolina didn’t. 

During the games, low-seeded teams sometimes outperform the higher seeded teams, which is why you should never ignore the underdogs. Just because the committee ranks one team over another doesn’t necessarily mean it’s the better team.

Bettors learned long ago to set odds for at least one underdog. This year, 19 teams were listed as possible Cinderella teams. In alphabetical order, these are: 

• • • • • Arizona State
        • Charleston
        • Colgate
        • Furman
        • Grand Canyon
        • Howard
        • Iona
        • Kennesaw State
        • Kent State
        • Louisiana-Lafayette
        • Montana State
        • Nevada
        • Northern Kentucky
        • Oral Roberts
        • Texas A&M-Corpus Christi
        • Texas Southern
        • UC Santa Barbara
        • UNC Asheville 
        • Vermont

Scout the coaches and look for their experience as well as the teams’ experience. This might help you place your bets on the lucky underdog. Some bettors don’t feel like doing all the legwork, and bet a smaller sum like $100 on each underdog.

This technique doesn’t seem to be particularly reliable. Your outcome will range from tournament to tournament. Even with a lot of upsets, you won’t earn that much, and if the committee ranks hold up, you’ll likely lose the money. 

Hindsight is often 20/20 with underdogs, so you could take inspiration from past March Madness runs. Here are the 9 greatest underdog victories you should definitely keep in mind.

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9 Greatest March Madness Underdog Picks

1. Villanova Wildcats (1985)

This championship team is unforgettable in the eyes of many hoops fans. The match against the No. 1 seed Georgetown went down in history as the biggest March Madness upset with a 66-64 win. Villanova’s average record of 19-10 meant fans were expecting one of the biggest defeats in college basketball history. Yet, they shot over 78% from the field, which was a tournament record. Winning 66-64, Villanova is the only No. 8 seed to win the championship to date. 

2. UConn Huskies (2014)

A year prior, the Huskies were banned from tournament play because of poor academic performance ratings. In true Cinderella fashion, the team came back with a vengeance. With second-year Kevin Ollie as head coach, the team made its way to the Final Four and defeated the Florida Gladiators. They won the championship by defeating the Kentucky Wildcats 60-54.

3. CCNY Beavers (1950)

The team’s starting lineup included two black and three Jewish players, which caused a scandal at the time. Although we now know it would later redefine basketball, this decision gained no love from the poll voters. Despite the backlash, the Beavers pushed and won the NCAA title with an impressive victory over Bradley. Sadly, the controversy surrounding CCNY only got worse when seven players were charged for their involvement in a point-shaving scandal.

4. LSU Tigers (1986)

The LSU Tigers went down in history in 1986 as the team to break the record as the lowest-seeded team at No. 11 to reach the Final Four. This record was later matched by George Mason in 2006, VCU in 2011, Loyola in 2018, and UCLA in 2021. A lesser-known fact is the team pushed through a lot of obstacles to achieve their rank, including dealing with a chickenpox outbreak.

5. George Mason Patriots (2006)

As a No. 11 seed, the Patriots turned heads and broke records with an impressive 23 regular season wins under their belt. More impressively they managed to knock off the tournament’s No. 1 overall seed, UConn, and advance to the Final Four. The Patriots lost to Florida, but became the second double-digit seed behind the LSU Tigers to reach the Final Four. 

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6. NC State Wolfpack (1983)

If we’re talking underdogs, North Carolina State University always comes to mind. The Wolfpacks pushed through the season and even defeated the top-ranked and heavily-favored Houston Cougars to win the championship. Earning the nickname Cardiac Pack, the team became the first No. 6 seed in history to win the national title. 

7. Syracuse Orange (2003)

Known as the Syracuse Orangemen at the time, things didn’t start out bright for the team. After losing two guards, Syracuse started the season with a loss against Memphis. Despite this, Syracuse turned the tables around 13-3 in the Big East and went on to win their first national championship 81-78 against Kansas.

8. Kansas Jayhawks (1988)

The Jayhawks got off to a rocky 12-8 start, but managed to turn things around in the season’s second half. The team even defeated rival seed No. 4 Oklahoma much to the fans’ delight. Notably, head coach Larry Brown earned the Coach of the Year title after this season. He’s the only coach in basketball history to win both an NCAA national championship and an NBA title. 

9. Loyola Ramblers (2018)

Loyola made headlines in 1963 with what’s now known as the biggest blowout in March Madness history. In 2018, they gathered national limelight again with their Cinderella run. While they didn’t win the national championship, they exceeded all expectations as a No. 11 seed making it to the Final Four. 

Keep Up With All Seeding Odds 

With the top four seeds in the 2023 tournament Alabama, Houston, Kansas, and Purdue, you know it’s going to be a good ride. Tune in to find out whether your favorite underdog makes it to the Sweet 16 or scores a big upset.

If you’re traveling outside the States or living somewhere with restrictive Wi-Fi like a student dormitory, you might be unable to watch March Madness. 

Outside North America, March Madness underdog picks aren’t that popular, so you won’t find many TV channels or streaming services featuring the tournament. Restrictive Wi-Fi networks, on the other hand, simply block or throttle data-heavy websites to prevent network congestion and overcrowding. 

This doesn’t mean you’ll have to miss out on all the action. Simply use CyberGhost VPN to keep up with your favorite underdogs on any Wi-Fi network. Connect to one of our VPN servers and watch March Madness on any device from laptops to smartphones to Smart TVs. 

We have servers across 11 locations in the US, so you can easily find one suited to your needs. We also optimized our 10 Gbps servers for streaming, which means you won’t have to worry about buffering, freezing, or drops in video quality. Keep the game going with CyberGhost VPN!

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