Oladipo attended DeMatha High School in Hyattsville, Maryland. He performed well in his senior year, averaging 11.9 points, 10.3 rebounds, and leading the team to conference and city championships.

Oladipo was considered a solid, but not top-end high school recruit. ESPN rated him as a 3-star recruit and just the 53rd best player at his position. He turned down offers from schools such as Notre Dame, Maryland, and Xavier to play college basketball for the Indiana University Hoosiers.

In his first two years at Indiana, Oladipo’s most important contribution to the talented Hoosiers squad was his ability to effectively defend almost all perimeter players. He averaged over 1.5 steals per game over his college career. Between his freshman and sophomore season, his offensive role also expanded as he increased his scoring average from 7.4 to 10.9 points per game.

Oladipo’s third year was a breakout season for him. He was fourth in the NCAA in field goal percentage and averaged 13.6 points per game while leading Indiana to a Big Ten championship. He received numerous awards including Sporting News’ Men’s Basketball College Player of the Year, National Co-Defensive Player of the Year, and first-team All-American recognition.

After his junior year, Oladipo declared for the NBA draft.

Oladipo was drafted by the Orlando Magic with the second overall pick. He had a strong rookie year, playing both point guard and shooting guard, and logged a triple-double against the Philadelphia 76ers.  He participated in the NBA Rising Stars Challenge and finished second in Rookie of the Year voting. In his second year, Oladipo finished second at the dunk contest during the NBA All-Star weekend. The following year, Oladipo spent time both in starting and bench roles for the Magic and scored a career-high 45 points against the Cleveland Cavaliers.

In June 2016, Oladipo, Domantas Sabonis, and Ersan Ilyasova were traded from the Magic to the Oklahoma City Thunder for Serge Ibaka. He signed a 4-year, $84M contract extension with the Thunder. Oladipo missed 15 games through injury, but proved an effective scorer, averaging 16 points per game and posting the best three-point shooting percentage of his career up to that point.

In 2017, Oladipo was traded to the Indiana Pacers along with Domantas Sabonis in return for Paul George. The Pacers were expected to struggle after losing George, but Oladipo took a huge step forward and carried the team for much of the year. He scored 22 points in his Indiana debut, 35 points against his former team when the Pacers met the Thunder, and later achieved a new career-high with 47 points against the Denver Nuggets. The Pacers made the playoffs easily, where they lost a hard-fought series in seven games against LeBron James and the Cleveland Cavaliers, and Oladipo was awarded the league’s Most Improved Player award. He was also selected for the All-Star game, Third Team All-NBA, and First Team All-Defensive.

Oladipo missed several games throughout the first half of 2018-2019 with minor injuries, before rupturing a tendon in his right knee in January that left him sidelined until midway through the following season. He had played 13 games in 2020 after his injury rehab before the coronavirus pandemic suspended the season.