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Head coach John Calipari of the Kentucky Wildcats reacts to a play against the Auburn Tigers during the 2019 NCAA Basketball Tournament Midwest Regional at Sprint Center on March 31, 2019 in Kansas City, Missouri. (Christian Petersen/Getty Images/TNS) **FOR USE WITH THIS STORY ONLY**

Head coach John Calipari of the Kentucky Wildcats reacts to a play against the Auburn Tigers during the 2019 NCAA Basketball Tournament Midwest Regional at Sprint Center on March 31, 2019 in Kansas City, Missouri. (Christian Petersen/Getty Images/TNS) **FOR USE WITH THIS STORY ONLY**

LEXINGTON, Ky. - For decades, two losses had reigned as the most painful in Kentucky Wildcats men's basketball history.

The 72-65 loss to Texas Western in the 1966 NCAA Tournament championship game cut UK fans deeply. It cost a beloved Wildcats' team with no starter taller than 6-foot-5 a happy ending and denied an aging Adolph Rupp the fifth NCAA title he so craved.

Christian Laettner's famed buzzer beater in overtime that gave Duke a 104-103 win over Kentucky in the 1992 NCAA Tournament East Region finals was a crushing blow for UK's Unforgettables, the loyal four seniors who stuck with Kentucky through a crippling NCAA probation.

Thanks to television replays, Laettner's shot is a wound that never fully heals for the Big Blue Nation.

Yet as painful as those two losses were, the unanimous choice as the most agonizing UK basketball defeat of the John Calipari coaching era may exceed both on the scale of difficult Kentucky setbacks.

1. Wisconsin 71, Kentucky 64 (April 4, 2015) - Kentucky entered the 2015 Final Four two wins from an undefeated national title. The Wildcats were leading Wisconsin 60-56 with 6:35 left in the game, when UK's offense went AWOL.

A five-minute Cats' scoring drought that included three shot-clock violations opened the door for a veteran Wisconsin team. Led by Frank Kaminsky (20 points) and Sam Dekker (16), Bo Ryan's Badgers ended the bid for college basketball history by UK (38-1) before 72,238 fans in Lucas Oil Stadium in Indianapolis.

2. West Virginia 73, Kentucky 66 (March 27, 2010) - A gifted UK roster led by future NBA stars John Wall, DeMarcus Cousins and Eric Bledsoe suffered through a dreadful shooting game (4-of-32 three-pointers, 16-of-29 free throws) and was upset by Bob Huggins and West Virginia in front of 22,497 fans in the Carrier Dome in Syracuse in the 2010 NCAA Tournament East Region finals.

3. North Carolina 75, Kentucky 73 (March 26, 2017) - In an NCAA Tournament South Region finals showdown, the Tar Heels' Luke Maye sank a game-winning jumper just ahead of the final buzzer. Before 16,412 fans in the FedEx Forum in Memphis, De'Aaron Fox, Malik Monk, Bam Adebayo and Co. saw their season end one game short of the Final Four.

4. Connecticut 60, Kentucky 54 (April 7, 2014) - What had been an unexpected UK thrill ride through the 2014 NCAA Tournament ended with a thud in the national championship game. The Wildcats made only five of 16 three-pointers and missed 11 free throws (13-of-24) and lost to the Shabazz Napier-led Huskies before 79,238 fans at AT&T Stadium in Arlington, Texas.

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5. Connecticut 56, Kentucky 55 (April 2, 2011) - UConn star Kemba Walker (18 points, seven assists, six rebounds) and horrid UK shooting (21-of-62 field goals, 4-of-12 foul shots) spoiled the Wildcats' first Final Four trip since 1998 before a crowd of 75,421 at Reliant Stadium in Houston.

6. Duke 118, Kentucky 84 (Nov. 6, 2018) - In a gut punch to Big Blue pride, Duke freshman stars RJ Barrett (33 points), Zion Williamson (28 points) and Cam Reddish (22 points) obliterated UK in the 2018-19 season opener before 18,907 fans in the Bankers Life Fieldhouse in Indianapolis.

7. Auburn 77, Kentucky 71, OT (March 31, 2019) - To earn its first Final Four trip since 2015, Kentucky needed only to beat an Auburn team it had bested twice during the regular season. Bruce Pearl's Tigers were playing their first game since losing their most talented player, forward Chuma Okeke, to a torn ACL.

However, Auburn's veteran backcourt of Jared Harper (26 points) and Bryce Brown (24) dominated UK's all-freshman guards corps and the Wildcats again shot poorly from the foul line (12-of-21) on a big stage. As a result, the Cats fell in the NCAA Tournament Midwest Region finals before 17,174 fans at the Sprint Center in Kansas City.

8. Kansas State 61, Kentucky 58 (March 22, 2018) - The NCAA Tournament South Region broke wide open for the No. 5 seed Cats when the top four seeds were all eliminated during the tourney's opening weekend. UK was unable to take advantage, done in by poor shooting (16-of-42 field goals, 23-of-37 free throws) and physical K-State defense in the round of 16 before 15,616 fans in Atlanta's Philips Arena.

9. Indiana 73, No. 1 Kentucky 72 (Dec. 10, 2011) - Christian Watford's buzzer-beating three-pointer from the left wing not only upset No. 1 Kentucky. It also set off a raucous postgame court storm by many in the Assembly Hall crowd of 17,472. Combined, the experience was apparently so uncongenial for Calipari that UK refused to return to Bloomington to play and, as a result, the long-running UK-IU regular-season series ended.

10. Florida 69, Kentucky 52 (Feb. 12, 2013) - Kentucky's 2012-13 season ended in the NIT - and a big reason was what the crowd of 12,480 at the Stephen C. O'Connell Center in Gainesville witnessed. Kentucky freshman star Nerlens Noel ran into a basket support after blocking a shot and landed awkwardly. The result was a torn ACL in Noel's left knee. Without its talented big man, UK went 4-4 down the stretch and missed the NCAA Tournament.

Other losses receiving votes: Tennessee 82, Kentucky 78. 2019 SEC Tournament semifinals; South Carolina 72, Kentucky 67, 2013-14 regular season; Indiana 73, Kentucky 67, 2016 NCAA Tournament round of 32; Seton Hall 84, Kentucky 83, 2018-19 regular season; Texas A&M 79, Kentucky 77 (OT), 2015-16 regular season; LSU 73, Kentucky 71, 2018-19 regular season; Vanderbilt 64, Kentucky 48, 2013 SEC Tournament quarterfinals; Robert Morris 59, Kentucky 57, 2013 NIT opening round.

Visit the Lexington Herald-Leader (Lexington, Ky.) at www.kentucky.com

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