in 2012, ollie was named the 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. as an assistant coach in 2011, ollie helped guide the huskies to a record 11 straight postseason wins which included winning 5 games in 5 nights to win the big east tournament championship and winning the 2011 ncaa men's basketball championship. on december 29, 2012, uconn and ollie agreed to a five-year deal.