In 2012, Ollie was named the new head basketball coach at Connecticut, replacing longtime hall of fame coach Jim Calhoun. During his college career, Ollie had played under Calhoun -- he also served as an assistant coach for Calhoun's final two seasons at UConn.  He won his coaching debut on November 9, 2012 at the "Armed Forces Classic" played at Ramstein Air Base in Germany. Connecticut upset Michigan State 66-62. On December 29, 2012, UConn and Ollie agreed to a five year deal. The Huskies ended their season finishing 8th in Big East play (10-8) finishing 20-10 overall with quality wins over Cincinnati, Syracuse, Michigan State, and Notre Dame, despite being ineligible from postseason play. UConn ended their season ranked as high as 21st in the country.
The Huskies in the 2013-2014 season were eligible for postseason play. On November 8th, 2013, Ollie and the Huskies opened up their season with a win vs Maryland as they were ranked 17th in the country. On December 2nd, the Huskies earned a win over the Florida Gators. Following that week, Ollie and UConn made it to the top 10 in rankings as ranked number 9. The Huskies started 0-2 in their new conference (AAC) after losses to Houston and SMU, but earned their first conference win over UCF. They then went on to earn more conference wins on the road vs Memphis and Rutgers. In a game vs Louisville, Ollie was ejected after two technical fouls were given to him by referee Mike Stuart in less than 5 seconds, after a controversial no call. Ollie said after the game, "It was still a foul." Giffey, who plays for UConn, was hit by Louisville forward Wayne Blackshear after attempting a three pointer but no call was made, which made Kevin Ollie react and get ejected from the game. On February 15th, Ollie earned his 40th career win, which was the Huskies' 20th win of the year in an overtime win vs Memphis.
NBA player Kevin Durant in an interview with Grantland said that Kevin Ollie (who played for Oklahoma City Thunder in 2009-2010) "taught him the ropes", and "changed the culture of Oklahoma City". He also said, “Kevin Ollie, he was a game changer for us. I think he changed the whole culture in Oklahoma City. Just his mind set, professionalism, every single day. And we all watched that, and we all wanted to be like that. It rubbed off on Russell Westbrook, myself, Jeff Green, James Harden. And then everybody who comes through now, it’s the standard that you’ve got to live up to as a Thunder player. And it all started with Kevin Ollie.”
In an article in the New Haven Register, it was said that Ollie was signed to the Cleveland Cavaliers by then GM Jim Paxson "to tutor and mentor LeBron James. He can also be a good influence on our younger players, the primary one being LeBron himself."
National champion Conference regular season champion Conference regular season and conference tournament champion Division regular season champion Division regular season and conference tournament champion Conference tournament champion