His father, Butch Ryan was already a legend in the area, coaching youth sports including basketball to under-privileged children in Chester, Pennsylvania.

The center snapping him the ball was Ted Cottrell, who later served as a defensive coach and coordinator for a number of teams in the NFL.

He also won eight Wisconsin Intercollegiate Athletic Conference championships and set a Division III scoring defense record in 1997, with his team only allowing 47.5 points per game.

[3] Ryan also brought a 161 percent increase in home attendance at UWM, giving the program a new energy that continued into the tenure of his successor Bruce Pearl.

The coaching search began to concentrate on Rick Majerus of the University of Utah (who was a Milwaukee native) and Bo Ryan.

After Majerus pulled his name out of consideration, UW athletic director Pat Richter made the decision to hire Ryan as Wisconsin's 13th head coach.

The team, led by Kirk Penney, surprisingly finished in a four-way tie for the Big Ten regular-season title and received an invitation to the NCAA tournament.

In the 2004–05 season, Wisconsin advanced to the "Elite Eight" in the NCAA Tournament, losing to the eventual national champion North Carolina Tar Heels.

[1] On December 12, 2009, Ryan recorded his 200th victory as Wisconsin head coach by defeating in-state rival Marquette, 72–63 at the Kohl Center.

[9] On January 24, 2010, Ryan recorded his 100th Big Ten Conference victory by defeating Penn State, 79–71 at the Kohl Center.

[10] On March 9, 2012, in the 2012 Big Ten Conference men's basketball tournament quarterfinals the Badgers defeated the Hoosiers, giving Ryan his 266th win at Wisconsin and vaulting him past Bud Foster to become the winningest coach in school history.

[14] On February 14, 2015, Ryan was named a finalist to be considered for election in the Class of 2015 for the Naismith Memorial Basketball Hall of Fame.

He coached the Badgers to the NCAA Final Four two years in a row, falling to Kentucky, 74–73, in the 2014 semifinals in Arlington, Texas, and to Duke, 68–63, in the championship game on April 6, 2015, in Indianapolis.

[20] On December 15, 2015, Ryan announced his retirement after a win against Texas A&M–Corpus Christi, effective immediately, and Gard took over for the rest of the season.

Shortly after the Badgers' loss in the 2015 NCAA title game, there was speculation Ryan would retire when he and his wife put their home in Madison up for sale.

At a charity fundraiser, he explained that they had chosen to downsize now that their children were all adults and out of the house, and had bought a condo near the Badgers' home of the Kohl Center.