Playing in his seventh NBA season, Oladipo appeared in 19 regular-season games for the Pacers. His debut was delayed until late-January as he recovered from a quad injury suffered during the 2018-19 season. On Jan. 29, Oladipo took the floor in a win over the Bulls, finishing with nine points and four assists in 21 minutes. On Feb. 5, Oladipo returned to the starting lineup, playing 25 minutes and posting 13 points, two rebounds and two assists. Over a five-game stretch from Feb. 27 through Mar. 10, Oladipo averaged 18.6 points, 4.8 rebounds, 3.6 assists, and 1.4 steals per game. He topped out with 27 points in the Pacers' final game before the season was suspended on Mar. 11. In the Orlando bubble, Oladipo appeared in 10 of Indiana's 12 games. In a seeding-round win over the Lakers on Aug. 8, Oladipo went for 22 points, seven rebounds, and five assists in 35 minutes. Over four postseason contests against Miami, Oladipo averaged 17.8 points, 3.3 rebounds, 2.5 assists and 2.3 steals, while hitting better than 36 percent of his three-point attempts. In Game 4 of the series, Oladipo finished with 25 points, eight rebounds, five assists, and a playoff-career-high five steals.

Fresh off a career year and his first All-Star appearance in 2017-2018, Oladipo started his second season with the Indiana Pacers on a tear, averaging 22.0 points, 5.9 rebounds and 4.4 assists in October. He continued to shine through November, averaging 20.9 points, 7.4 rebounds and 5.0 assists per tilt. That stretch included four double-doubles, as well as a season-high 36 points in a loss to Philadelphia on Nov. 7. On Nov. 17, in a game versus Atlanta, Oladipo hurt his right knee and missed 11 games. He returned Dec. 12 and posted 12 points and 10 boards in a win over the Bucks. On Jan. 4, he matched his season high of 36 points in an overtime win at Chicago. But then right knee trouble struck once again. Oladipo suffered a ruptured quad tendon in his right knee 10 minutes into a Jan. 23 contest with the Toronto Raptors. The injury forced season-ending surgery. Oladipo was still named to the All-Star team, despite the injury. He ended up playing just 36 games for the Pacers, averaging 18.8 points, 5.6 rebounds and 5.2 assists. His per contest rebound and assist figures were both career highs. Oladipo also averaged 2.0 steals-plus-blocks per game. The electric guard has two more seasons remaining on his contract with the Pacers. Oladipo may miss games at the start of the 2019-20 season while he rehabs his knee.

Oladipo enjoyed a breakout season in 2017-2018, his fifth in the league and first with the Indiana Pacers. Oladipo started a career-high 75 games, parlaying his good health and good fortune into career-high averages of 23.1 points, 5.2 rebounds and 4.3 assists per contest. Oladipo finished 10th in the NBA in scoring. Unsurprisingly, Oladipo posted the best shooting percentages of his career from the field (47.7 percent) as well as three-point range (37.1 percent). He poured in a career-high 47 points against Denver on Dec. 10. He also continued his mastery on the defensive end, leading the NBA in steals at 2.4 thefts per tilt. The Pacers met LeBron James and the Cleveland Cavaliers in Round 1 of the NBA playoffs, and Oladipo nearly matched King James. Oladipo tallied a triple-double in Game 6, then scored 30 points in Game 7 of a 105-101 loss. He was named in the All-NBA Third Team and was also selected as the league's Most Improved Player for the 2017-18 season.

Oladipo was traded from the Magic to the Thunder on June 23, 2016, and he signed a four-year contract extension with Oklahoma City on Oct. 31. During his first season with his new team, Oladipo averaged 15.9 points, 4.3 rebounds, 2.6 assists and 1.2 steals in 33.2 minutes across 67 games (all starts). He also shot career highs in field-goal percentage (.442) and three-point percentage (.361). Oladipo's best stretch of the season was a six-game period from Feb. 15 through Mar. 16. He averaged 20.5 points on 14.5 shots, plus 3.8 rebounds, 1.8 assists and 1.2 steals in 31.4 minutes. His best individual performance of the season was one of his three double-doubles, which occurred during a two-point win over the Rockets on Nov. 16. Oladipo played 40 minutes and recorded 29 points (12-18 FG, 5-7 3Pt), 10 rebounds, five assists and two steals. The Thunder finished the season 47-35, making the playoffs but losing in the Western Conference First Round to the Rockets in five games. During the series, Oladipo averaged 10.8 points, 5.6 rebounds, 2.0 assists and 1.4 steals. His best playoff performance was during Game 4, where he posted 15 points (7-10 FG, 1-3 3Pt), four rebounds, two assists, two steals and one block with no turnovers in 39 minutes during the four-point loss.

Oladipo played 72 games (52 starts) in 2015-16 -- his age-23 season and his third with the Magic. He averaged 16.0 points, a career-high 4.8 rebounds, 3.9 assists and 1.6 steals in 33.0 minutes. Oladipo's 1.6 steals ranked 19th in the NBA. He also set career marks in field-goal percentage (43.8), three-point percentage (34.8), free-throw percentage (83.0). In addition, Oladipo set new single-game career marks in points (45) and blocks (four). His 45-point effort was his best overall performance of the season, and he shot 16-of-22 from the field, 6-of-7 from three and 7-of-8 from the charity stripe while also posting five rebounds, three assists, three steals and two blocks. Plus, Oladipo had two double-doubles and one triple-double. His best stretch of the season was a 10-game span from March 2 to March 21. Oladipo averaged 23.7 points on 16.5 shots per game, plus 5.3 rebounds, 3.3 assists, 2.0 steals and 1.4 blocks across 37.4 minutes. Despite Oladipo's efforts, the Magic was left out of the postseason due to a 35-47 regular-season mark.

Oladipo played 72 games (71 starts) with the Magic during his second season in the NBA. He averaged career highs in points (17.9), rebounds (4.2), steals (1.7), field-goal percentage (43.6), three-point percentage (33.9) and free-throw percentage (81.9). He also dished out 4.1 assists in 35.7 minutes per contest. In addition, Oladipo set new single-game highs with 38 points and 13 rebounds. Arguably his best performance of the season was Mar. 6 during a five-point win over the Kings. Oladipo posted 32 points (14-24 FG, 2-3 3Pt, 2-2 FT), 10 assists, five steals and three rebounds. It was one of his three double-doubles. One of Oladipo's best stretches of the season was seven games from Feb. 27 through Mar. 11. He averaged 22.7 points on 18.0 shots, plus 5.3 assists, 3.3 rebounds and 2.4 steals in 38.6 minutes. The Magic finished the season 25-57, but it was clear they had a core building block in Oladipo.

Following three years at the University of Indiana, Oladipo was selected with the second overall pick in the 2013 NBA Draft by the Orlando Magic. He made his NBA debut during the first game of the season, a loss to the Pacers on Oct. 29. Oladipo came off the bench, played 23 minutes and posted 12 points (4-11 FG, 1-2 3Pt, 3-5 FT), three rebounds, two assists and one steal. On the season, he played 80 games (44 starts) and averaged 13.8 points, 4.1 rebounds, 4.1 assists and 1.6 steals in 31.1 minutes per contest. He also ranked ninth in The Association in total steals (129) and steal percentage (2.7). Overall, he was voted onto the All-Rookie First Team. The Indiana product recorded his first career triple-double on Dec. 3 during a close loss at Philadelphia. In the loss, Oladipo tallied 26 points, 10 rebounds, 10 assists and three steals. On Jan. 15, the rookie scored a season-high 35 points, to go with eight assists, four rebounds and three steals, during a home loss to the Bulls. His best performance of the season was during an eight-point win over the Knicks on Feb. 21. Oladipo posted 30 points (11-23 FG, 2-3 3Pt, 6-6 FT), 14 assists, nine rebounds and two steals. For the season, Oladipo accumulated seven double-doubles and one triple-double.