A No. 14 seed has upset a No. 3 a total of 22 times in the first round of the NCAA Tournament, although it hasn't happened since Abilene Christian edged Texas by a point in 2021. Prior to that, it hadn't occurred since 2016 with Stephen F. Austin taking out West Virginia. But a 14 seed beating a 3 is still twice as likely as a No. 15 knocking off a No. 2, which has happened only 11 times.

Since the NCAA Tournament expanded to 64 teams, there have been 19 years where at least one 14 seed has triumphed over a 3 but only two 14 seeds have ever advanced past the second round: 1986 Cleveland State and 1997 Chattanooga. All the 14 seeds this year are mid-majors as well, and I don't expect any to get to the Sweet 16 should they pull the first-round upset.

The biggest spread upset in a 14 beating a 3 is 14 points: Stephen F. Austin was that big of a 'dog eight years ago and Ohio was the same in 2010 when it beat Georgetown. The lone 14 over 3 upset to see overtime was Old Dominion over Villanova in 1995, and it went to three OTs.

No school has ever lost as a No. 3 to a No. 14 more than once, but Weber State has won two opening-round games as a 14 seed (1995 vs. Michigan State and four years later vs. North Carolina). The Wildcats are not in this year's Dance. In 2023, only one No. 14 seed managed to stay within single digits of a No. 3 and that was Kennesaw State losing by five to Xavier

Let's dive into each No. 3 vs. No. 14 matchup and isolate the best chance for an upset.

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14 vs. 3 upset rankings

Ordered from least likely to most likely.

4. Oakland over Kentucky (-13.5)

I have Kentucky winning the South Region, so the Wildcats better not lose to Horizon League regular season and tournament champion Oakland, which is located near Detroit, not near San Francisco. The Golden Grizzlies had the Horizon League Player of the Year in Trey Townsend as well as the Sixth Man of the Year in Jack Gohlke. But they should be overwhelmed by UK's size as the Cats have three 7-footers, while Oakland's tallest player is 6-foot-9. 

The best power conference teams the Golden Grizzlies played this season were Illinois, Michigan State and Dayton, and Oakland lost each by at least 11 points. In addition, it's not like Oakland had to beat the best of the best to win the Horizon League Tournament, defeating the No. 6, 7 and 8 seeds. It's the first-ever meeting between these programs but Kentucky is 12-0 all-time against Horizon League opponents. The Cats are 26-2 in their past 28 opening-round games. They are a No. 3 seed for the fourth time and won in Round 1 in each of the previous three. 

3. Morehead State over Illinois (-12)

Illinois is in my East Region final against No. 1 overall seed UConn. The Illini can score with anyone with their stellar 1-2 punch of Terrence Shannon Jr. and Marcus Domask, with Shannon's 102 points scored in the Big Ten Tournament the second-most by a player in a season in that event's history. He became one of 11 players to average at least 30 points a game (minimum three games) since at least 1996-97 and is one of only three players to do it in a power conference tournament, joining Kevin Durant at Texas (2007) and Doug McDermott at Creighton (2014). Illinois is one of only three Big Ten teams – and one of 14 teams nationally – to earn a bid in each of the last four NCAA Tournaments. 

Morehead State was the Ohio Valley Conference regular season and tournament champion led by OVC Player of the Year Riley Minix and fellow All-OVC first-team pick Jordan Lathon. The Eagles set a school record with 26 wins and are in the NCAA Tournament for the ninth time. They were also a No. 14 seed the last time in 2021 and were blown out by West Virginia. Morehead State actually played three Big Ten schools this season, losing by 30 at Purdue, by 23 at Penn State and by one at Indiana. MSU might be rather rusty considering the OVC title game was back on March 9 -- it earned the nation's first automatic bid. 

2. Akron over Creighton (-12.5)

Akron is incredibly fortunate to be dancing thanks to a devastatingly bad foul in the final seconds of the Mid-American Conference Tournament title game by Kent State's Julius Rollins -- think Chris Webber with that infamous timeout for Michigan in the 1993 national title loss to North Carolina. Kent State had just scored to take a one-point lead, but Rollins thought his team will still trailing so he fouled with 4.6 seconds left. Akron hit both free throws to win the game. The Zips are led by MAC Player of the Year Enrique Freeman; he was a unanimous selection by the 11 opposing head coaches. The 6-foot-7 forward is a double-double machine and leads the country with 30 of them. It's the sixth trip to the Dance for Akron, which lost in the first round of the previous five. 

You could make an argument that Creighton has the nation's best trio of players in guards Baylor Scheierman (18.4 PPG, 9.0 RPG) and Trey Alexander (17.6 PPG, 5.7 RPG, 4.8 APG) and big man Ryan Kalkbrenner (17.1 PPG, 7.4 RPG, 3.0 BPG). The Bluejays are the only team to have beaten No. 1 overall seed UConn since Christmas and did so by 16 in Omaha. Where Creighton might get into trouble is if one of its big three gets into foul trouble (or injured) as there's not much depth. The Bluejays have won at least one game in 12 of their last 14 postseason appearances. Creighton's No. 3 seed matches the program's best in history (also in 2014). 

1. Colgate over Baylor (-13.5)

I like Baylor as it has six players averaging double-figure points, but I think the Bears are clearly the worst No. 3 seed with their 10 overall losses -- including double-digit defeats to Iowa State and Texas Tech in two of their past three games. There's also a potential distraction around Coach Scott Drew as Louisville is reportedly pushing hard to hire him. Baylor has earned a top-three seed for a fourth straight NCAA Tournament, the only school in the country to say that. It was also a No. 3 seed last year and had little trouble in the opening round vs. No. 14 UC Santa Barbara

Yet again, Colgate was the Patriot League regular season and conference tournament champion as the Raiders have truly owned the league for years. Braeden Smith was the Patriot League Player of the Year. Colgate is one of the top defensive teams in the country, ranking 11th in scoring defense (63.2), 13th in 3-point field goal defense (29.8), 24th in defensive rebounds per game (27.8), and 29th in field goal percentage defense (40.8). Baylor has had its issues defensively this season at times. 

The Raiders also played three power conference schools during the season, losing by four at Syracuse, by 27 at Arizona and by 17 at Illinois. Those latter two might be Final Four teams. It's the seventh Big Dance for Colgate and it is 0-6. This is the third time Colgate has been a No. 14 seed.