He began playing basketball as a young child, with the help of his mother, who made a ball for him by stuffing rags into a gunnysack.

[5][6] Rupp began his career in coaching by accepting a teaching job at Burr Oak High School, Kansas.

After a one-year stay, Rupp moved on to Marshalltown, Iowa, where he coached wrestling, a sport he knew nothing about at the time and learned from a book.

During his four years at Freeport, Rupp compiled a record of 66–21 and guided his team to a third-place finish in the 1929 state tournament.

[citation needed] University of Illinois head basketball coach Craig Ruby was invited to speak at the team banquet following the 1929–30 season.

[10] In his 41 seasons as UK coach, Rupp coached 32 All-Americans, chosen 50 times, 52 All-SEC players, chosen 91 times, 44 NBA Draft Picks, 2 National Players-of-the-Year, 7 Olympic Gold Medalists, and 4 Naismith Memorial Basketball Hall of Fame members.

On October 20, 1951, former Kentucky players Alex Groza, Bill Spivey, Ralph Beard, and Dale Barnstable were arrested for taking bribes from gamblers to shave points during the National Invitation Tournament game against the Loyola Ramblers in the 1948–49 season.

[13] Rupp and the university were criticized by the presiding judge, Saul Streit, for creating an atmosphere for the violations to occur and for "failing in his duty to observe the amateur rules, to build character, and to protect the morals and health of his charges".

[15] A subsequent NCAA investigation found that Kentucky had committed several rule violations, including giving illegal spending money to players on several occasions, and also allowing some ineligible athletes to compete.

It featured Kentucky's all-white team against Texas Western's all-black starting five, and took place at the height of the Civil Rights Movement.

The game, which Texas Western won 72–65, helped accelerate the ongoing integration movement in college basketball, as well as the overall recruiting approach of the SEC, ACC, and SWC conferences.

Rupp was very demanding of his players, constantly putting extreme pressure on them in practice, and mercilessly berating them for any mistakes.

The depth of his superstitious nature was revealed while he was coaching at Freeport, when he had bought a new blue suit to replace his old brown one.

[26] Rupp signed his first black player, troubled 7'2" center Tom Payne, who played in the 1971 season.

After his lone varsity season, Payne, who was on the verge of flunking out of school, joined the NBA's first-ever supplemental draft.

In September 1973, Rupp was hired as Vice President of the Board of the Kentucky Colonels of the American Basketball Association.

Rupp Arena, the current home of the Kentucky men's basketball team, is named in his honor.