This year’s March Madness tournament reignited a rivalry between two of college basketball’s most renowned coaches that spans decades and multiple teams.
Rick Pitino and John Calipari’s rivalry began in the early 1990s, when Pitino was the head coach for the University of Kentucky, and Calipari was the head coach for the University of Massachusetts. They first met in the 1992 NCAA Tournament’s Sweet 16, where Pitino’s Wildcats defeated Calipari’s UMass Minutemen 87-77. This victory gave the Kentucky Wildcats a spot to the Elite Eight and was the first of many battles between the two rivals. Calipari began making a name for himself, while Pitino established the Wildcats as a perennial powerhouse.
Their paths crossed again in the 1996 Final Four, one of the most memorable encounters in the rivalry. Pitino’s Wildcats, featuring future NBA stars like Antoine Walker and Tony Delk, took down Calipari’s UMass team 81-74. Kentucky went on to win the national championship that same year, Pitino capped off an outstanding 34-2 season. It was another bitter defeat for Calipari, but his ability to guide UMass to the Final Four demonstrated his coaching potential and determination to compete at the highest level, this was the first battle of many.
The rivalry took on a new twist in 2023 when Pitino returned to the college game as the head coach of St. John’s University, determined to resurrect the former glory of the program. On the other hand, in 2024, Calipari left Kentucky to coach Arkansas, where he wanted to prove he is still an elite coach after exiting in the first round in the past two years. Fans and analysts speculated whether the two would cross paths again, and fate answered during the 2025 NCAA Tournament.
This year, in the Round of 32, Calipari’s 10th-seeded Arkansas Razorbacks stunned Pitino’s second-seeded St. John’s Red Storm with a convincing 75-66 victory on Mar. 22. The win advanced Arkansas to the Sweet 16, adding another chapter to the rivalry. This victory marked Calipari’s third consecutive NCAA Tournament win over Pitino since the 2012 Final Four, bringing Calipari’s March Madness record against Pitino to 3-2.
A few years after their encounter in the Final Four, the competition between Pitino and Calipari would soon shift to a new battleground: the state of Kentucky itself. After a stint in the NBA with the Boston Celtics, Pitino returned to college basketball to take the helm at Louisville in 2001. Meanwhile, despite building a powerhouse program at Memphis, and leading them to the national championship game in 2008. In 2009, Calipari took over as the head coach at Kentucky, the rivalry was within the same state.
From 2009 to 2017, their teams faced off every year in one of college basketball’s most anticipated showdowns: the Kentucky-Louisville rivalry. Calipari’s Wildcats usually held the upper hand, including a notable victory in the 2012 Final Four when Kentucky defeated Louisville 69-61. Kentucky later on would win the national championship that same year, adding another layer of defeat for Pitino.
The two met again in the 2014 Sweet 16, with Kentucky narrowly escaping Louisville’s attempt at an upset in a 74-69 win. Calipari again advanced, eventually leading Kentucky to the national championship game, where they fell short against UConn. Although Pitino and Louisville have secured a few regular-season victories, Calipari’s dominance in the NCAA Tournament cemented his legacy as the superior postseason tactician.
Ore Odutanya, a senior varsity basketball player from Guilderland, N,Y., believes Calipari’s recruiting methods has evolved with the transfer portal.
“The game has evolved and Calipari also looks for players in the transfer portal nowadays,” he said. “You can’t just have five freshman starting in the Final Four, it’s just not going to happen. I think that [Calipari‘s] new recruiting methods will allow Arkansas to make deep runs within the [NCAA] tournament in the future.”
Beyond college basketball, the rivalry even extended briefly into the NBA. Pitino coached the Boston Celtics from 1997 to 2001, while Calipari led the New Jersey Nets from 1996 to 1999. Their NBA tenures were less successful compared to their college achievements, but their head-to-head matchups continued, with each coach securing three wins in their six meetings.
Jack Wilson, a junior boarder from San Francisco, Calif., had St. John’s beating Arkansas in his March Madness bracket.
“I thought St. John’s was a lock to beat Arkansas because I thought Rick Pitino brought in great players through the transfer portal,” he said. “I was really disappointed in RJ Luis’ performance in that game, but I thought the media hated on him a little too hard.”
In the game against Arkansas, Big East Player of the Year RJ Luis Jr. hit two free throws with 4:56 left on the clock to put St. John’s within two points. Coach Pitino then subbed him out of the game. This was because Luis had only totaled nine points on 3-for-17 shooting.
Nasheen Gibbs, a senior border from Newark, N.J., thought St. Johns would beat Arkansas.
“I forgot Arkansas had Johnell Davis. Based on what I saw on Instagram, everyone made [St. John’s] looked like a final four lock, and I never thought they would lose to the 10th seed Arkansas,” he said.
The two coaches have expressed mutual respect over the years despite their competitive nature. Before their 2025 tournament encounter, in an interview conducted by Fox Sports on March 21, Pitino praised Calipari’s coaching.
“I don’t know a whole lot about him except he’s a terrific basketball coach,” Pitino said, Calipari, in turn, reflected on their parallel journeys in a press conference on March 26, noting, “He’s on chapter two of his new book, and we’re on chapter one.”
Overall, Pitino and Calipari have faced each other 28 times, with Calipari beating Pitino with a 16-12 record. Four games came in the NCAA Tournament, with each coach winning twice. Their rivalry remains one of the most captivating stories in college basketball history.
