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If you want to look like a genius in your bracket pool and predict a huge upset, picking a 14 seed over a three seed is probably your best bet. It's still not likely, but a 14 seed has pulled a first-round upset 23 times in 156 chances. Those are much better odds than a 16 seed winning (which has happened twice) or a 15 seed advancing past the first round (11 times).

Another thing in your favor is that a 14 seed getting a win in the men's tournament is becoming more common. The upset has happened five times in the last nine tournaments. You only have to look back to last year's tournament when Horizon League champion Oakland sent No. 3-seeded Kentucky home early 80-76.

The reason a 14 beating a three is more common than a 15 or 16 winning is seeding. Teams that tend to be put on the 14 line are from conferences like the Horizon, WAC, Sun Belt or CAA. There are quality mid-major teams in those conferences that have a puncher's chance in March.

Since the field expanded to 64 teams in 1985, a 14 seed has defeated a No. 3 seed in 20 of the 39 men's tournaments. Will it happen again this year? Let's dive into each 3-14 matchup and isolate the best chance for a takedown.

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14 vs. 3 upset rankings

Ordered from least likely to most likely.

4. Montana over Wisconsin

This is a terrible draw for Montana. I was actually looking to go against Wisconsin in the first round, but the Grizzlies aren't the team to give them trouble.

The Big Sky was down this season, and Montana still struggled defensively. The Grizz can't stop a nosebleed, and when they faced tougher competition earlier in the year, they allowed 95 to Utah State, 92 to Tennessee and 79 to Oregon.

Wisconsin should cruise to an easy victory.   

3. UNC Wilmington over Texas Tech

I need to apologize to the Seahawks. Before the field was announced, I posted on social media that UNC Wilmington was my upset special but ended with, "Just don't be Texas Tech." Darn it.

The Seahawks are an experienced, deep team that can cause problems for bigger schools with their style of play. However, Texas Tech is a tough matchup because the Red Raiders' deadly long-range shooters will likely exploit UNC Wilmington's leaky perimeter defense.

If the Seahawks played Wisconsin, I probably would have picked the outright upset. But Texas Tech is just a bad draw for them. 

2. Lipscomb over Iowa State

One thing a team typically needs to do in order to pull a big upset is make shots. Lipscomb can certainly make shots.

The Bisons rank 46th in three-point field goal percentage, 21st in two-point field goal percentage and seventh in free-throw percentage on KenPom. Any team shooting the ball that well has a puncher's chance, even against Iowa State's elite defense.

Where Lipscomb might struggle is on the defensive end. The Bisons played two SEC teams earlier in the season, and allowed 76 to Arkansas and 98 to Kentucky.

This is an interesting game, though, given how efficient Lipscomb is on offense. Iowa State also isn't healthy. The Cyclones will be without star Keshon Gilbert, who leads the team in minutes and assists and is second in scoring (13.4 points per game). Iowa State is definitely on upset alert.

1. Troy over Kentucky

I ranked this game No. 1 because Troy is talented for a mid-major team, and Kentucky feels vulnerable with all of its injuries. 

The Wildcats lost guard Jaxson Robinson for the season, and Lamont Butler was injured in the SEC Tournament. Butler has dealt with injuries all season, and his status for the first round is unknown. The Wildcats just aren't the same team without Butler because he runs Kentucky's offense. 

Troy ended the year hot, winning its last six games and blowing out all three opponents in the Sun Belt Tournament. The Trojans have the guards to get to the basket and take advantage of a Kentucky defense that ranks 289th in two-point field goal percentage. If you don't follow college basketball metrics, that's really bad. 

I actually picked Troy to pull the outright upset in my brackets. Wildcats coach Mark Pope took BYU to the tournament twice, and the Cougars never got past the first round. I think that trend might continue this season with Kentucky.