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. He led the Marshalltown team to a state wrestling title in 1926.

In 1926–30, Rupp accepted the basketball head coaching position at Freeport High School, (Freeport, Illinois) where he also taught history and economics. 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. While at Freeport High School Rupp started William “Mose” Mosely, the first African-American to play basketball at Freeport and the second to graduate from the school.

Rupp coached the University of Kentucky men’s basketball team from 1930 to 1972. There, he gained the nicknames, “Baron of the Bluegrass”, and “The Man in the Brown Suit”. Rupp’s Wildcat teams won four NCAA championships (1948, 1949, 1951, 1958), one National Invitation Tournament title in 1946, appeared in 20 NCAA tournaments, had six NCAA Final Four appearances, captured 27 Southeastern Conference regular season titles, and won 13 Southeastern Conference tournaments. Rupp’s Kentucky teams also finished ranked #1 on six occasions in the final Associated Press college basketball poll and four times in the United Press International (Coaches) poll. In addition, Rupp’s 1966 Kentucky squad—nicknamed “Rupp’s Runts”— finished runner-up in the NCAA tournament and Rupp’s 1947 Wildcats finished runner-up in the National Invitation Tournament. Rupp’s 1933 and 1954 Kentucky squads were also retroactively named national champions by the Helms Athletic Foundation; his 1934, 1947, and 1948 teams were retroactively named the national champion by the Premo-Porretta Power Poll.

Rupp was the head coach at Kentucky during the point shaving scandal of 1951. 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. This game occurred during the same year that Kentucky won their second straight NCAA title under Rupp. 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”. Rupp denied any knowledge of the point shaving and no evidence was ever brought against him to show he was connected to the incident in any way.

Rupp hired assistant coach Neil Reed in 1960 to help recruit African-American players and once asked the UK president to leave the SEC so he could recruit black players. Rupp tried his best to sign in-state black players Wesley Unseld and Butch Beard before both picked Louisville. Rupp recruited his first black player, troubled 7-2 center Tom Payne, who played in the 1970-71 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.

Rupp was forced into retirement in March 1972, at the age of 70. At the time, this was the mandatory retirement age for all University of Kentucky employees.

In April 1972, Rupp was named Team President of the Memphis Pros, soon to become the Memphis Tams, of the American Basketball Association.

In June 1973 Rupp quit as Tams president, calling the ABA “bush league” and saying it “would never survive”. Three months later, Rupp was hired as Vice President of the Board of the Kentucky Colonels of the American Basketball Association.

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. He was a 5-time National Coach-of-the-Year award winner, and a 7-time Conference Coach-of-the-Year award winner. Rupp was inducted into the Naismith Memorial Basketball Hall of Fame, College Basketball Hall of Fame, Kentucky Athletic Hall of Fame, Kansas Athletic Hall of Fame, University of Kentucky Athletic Hall of Fame, and Helms Athletic Foundation Hall of Fame. Further, since 1972, the Adolph Rupp Trophy, considered one of the nation’s premier basketball awards, has been given by the Commonwealth Athletic Club to the top men’s college basketball player. In addition, the University of Kentucky retired a jersey in his honor in the rafters of Rupp Arena, a 23,500-seat arena named after him, dedicated in 1976.

Rupp was born September 2, 1901 in Halstead, Kansas to Heinrich Rupp, a German immigrant, and Anna Lichi, a Palatinate (Quirnheim, Germany) immigrant. The fourth of six children, Rupp grew up on a 163-acre farm that his parents had homesteaded. 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. “Mother sewed it up and somehow made it round,” he recalled in 1977. “You couldn’t dribble it. You couldn’t bounce it either.”

Rupp died of spinal cancer at age 76 in Lexington, Kentucky, on December 10, 1977, on a night when Kentucky defeated his alma mater, Kansas, at Allen Fieldhouse in Lawrence, Kansas. The game that night was promoted as “Adolph Rupp Night”. He is buried in Lexington Cemetery. Rupp Arena, the current home of the Kentucky men’s basketball team, is named in his honor.

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. As a result, the Southeastern Conference voted to ban Kentucky from competing for a year and the NCAA requested all other basketball-playing members not to schedule Kentucky, with eventually none doing so. Because of these actions, Kentucky was forced to cancel the entire 1952–53 basketball season. Years later, Walter Byers, the first executive director of the NCAA, unofficially referred to this punishment as the first de facto NCAA death penalty, despite the current rule only coming into effect in 1985. The NCAA’s website similarly stated “In effect, it was the Association’s first “death penalty,” though its enforcement was binding only through constitutional language that required members to compete against only those schools that were compliant with NCAA rules. Despite fears that it would resist, Kentucky accepted the penalty and, in turn, gave the NCAA credibility to enforce its rules.”

In a 2009 interview with The New York Times, former University of Georgia basketball player Tim Basset alleged that Rupp had threatened him after a 1972 win against Kentucky, stating that Basset, who was Black, did not belong in the Southeast Conference, and that “We’ll get you back when you come to Lexington.” A month later, Basset and his team arrived in Lexington to play the Wildcats, and in UK’s gym, found an effigy of Basset hanging from the ceiling.