Whether you’re an experienced college basketball betting enthusiasts or a casual fan that only wagers when the annual national championship tournament rolls around, you’re probably like every other March Madness college hoops betting enthusiast these days – meaning, you’re in search of some value-packed upsets.
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Thankfully, that’s where I come in with some expert predictions on a quartet of first-round matchups that all look like ‘upset specials’ just waiting to happen!
Now, let’s get started.
2019 March Madness First Round Upsets Prediction
“It’s one game at a time.”@CoachWillyUVA discusses the #MarchMadness preparations. 🔶⚔️🔷 #GoHoos pic.twitter.com/qew8SdAZRa
— Virginia Men’s Basketball (@UVAMensHoops) 18 de marzo de 2019
No. 16 Gardner-Webb vs. No. 1 Virginia
- When: Friday, March 22, 2019, 3:10 PM ET
- Where: Colonial Life Arena, Columbia, South Carolina
- 2019 March Madness Odds: Virginia -23.5
Virginia is in the exact same spot they were a year ago when they took on No. 16 UMBC in the first round and now, we all know how that worked out. The Cavs lost to become the first No. 1 seed in NCAA tournament history to lose to a No. 16 seed. While Virginia leads the nation in fewest points allowed (55.1 ppg), but the Cavaliers also struggle to score the ball (71.8 ppg, 193rd) just like they did in their 69-59 ACC tournament loss to Florida State the last time out.
Gardner-Webb has won five straight and eight of their last nine games overall and the Runnin’ Bulldogs rank a fantastic 13th nationally in field goal shooting percentage (48.8%) and even more impressive 12th in three-point shooting (39.1%). Gardner-Webb has shot 50 percent or better in a stunning 16 games this season.
Keep in mind, Virginia has gone 0-4 ATS in their last four NCAA Tournament games while Gardner-Webb has gone a polar-opposite 4-0 ATS in their last four games following either a SU or ATS win while also going 9-2 ATS in their last 11 games against a team with a winning percentage above .600.
No. 12 Liberty (28-6) vs. No. 5 Mississippi State
- When: Friday, March 22, 2019, 7:27 PM ET
- Where: SAP Center, San Jose, California
- 2019 March Madness: Mississippi State -6.5
Mississippi State may have the higher seed in this opening round matchup, but hell, No. 12 seeds now have a rock-solid history of upsetting their fifth-seeded opponents. In addition to that, Mississippi State has really struggled in dropping three of their last five games while Liberty has won five straight and nine of their last 10 games overall.

I know the Flames don’t play the best competition in the world in the Atlantic Sun, but I’m smelling an upset just waiting to happen in this one and apparently 56 percent of public bettors are backing Liberty right now. Mississippi State is just 2-5 ATS in their last seven neutral site game while Liberty has gone 4-0 ATS in their last four games against a team with a winning percentage above .600.
No. 13 UC-Irvine (30-5) vs. No. 4 Kansas State (25-8)
- When: Friday, March 22, 2019, 2:00 PM ET
- Where: SAP Center, San Jose, California
- 2019 March Madness Odds: Kansas State -4.5
I know K-State won a share of the Big 12 regular season title and have an elite defense that ranks a stupendous third in points allowed nationally (59.2 ppg), but the Wildcats also struggle to score the ball and average just 65.8 points per game offensively (323rd). Conversely, UC-Irvine also has an elite defense that limits the opposition to just 62.3 points per game (20th), but the Anteaters have a better offense that puts up 72.9 points per contest (163rd).
More importantly, UC-Irvine has won a blistering 16 straight games including their overpowering 92-64 smackdown of Cal-State Fullerton in the Big West conference championship on Saturday. K-State is just 1-6 ATS in their last seven non-conference games while UC-Irvine has gone 6-0-1 ATS in their last 7 games following a straight up win of more than 20 points and a near-perfect 9-1-1 ATS in their last 11 games overall. A 61 percent of public bettors are backing the Anteaters to cover the chalk in this first round showdown.
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