Olawale played two seasons at El Camino College as a tight end, recording 15 receptions for 338 yards and three touchdowns. As a junior, he transferred to the University of North Texas, where he was switched to H-back, recording seven receptions for 79 yards. In his senior season, he was moved to wide receiver, appearing in eight games and recording two receptions for nine yards.
After not being selected in the 2012 NFL Draft, Olawale received a tryout invitation for rookiemini-camp where he was converted from wide receiver to full back, and performed well enough to be signed as an undrafted free agent on May 14. Although he enjoyed a successful preseason, he was waived on August 31, after the team decided to keep Phillip Tanner. Olawale was then signed to the team's practice squad.
On December 4, 2012, the Oakland Raiders hampered by injuries to running backsDarren McFadden and Mike Goodson, signed Olawale from the Dallas Cowboys practice squad. He appeared in three games during the season as a fullback. Olawale became a core special teams player. In 2013, he recorded eight special teams tackles. In addition, he had seven receptions for 63 yards in the 2013 season. The next year, he led the team with 14 special teams tackles. On December 21, 2014, he scored his first professional touchdown against the Buffalo Bills. In the next game, he had another receiving touchdown, this time against the Denver Broncos. He finished the 2014 season with five receptions for 18 yards and two touchdowns. On December 8, 2015, he was signed to a three-year contract extension. On November 8, against the Pittsburgh Steelers, he had a 19-yard rushing touchdown. He finished the 2015 season with 10 special teams tackles, which led the team. He finished the 2015 season with 24 carries for 110 rushing yards and a rushing touchdown to go along with nine receptions for 84 yards. On November 21, 2016, against the Houston Texans, he had a 75-yard receiving touchdown from quarterback Derek Carr in the 27–20 victory at Azteca Stadium. Overall, he finished the 2016 season with 17 carries for 47 rushing yards to go along with 12 receptions for 227 receiving yards and a receiving touchdown. His production dipped in the 2017 season but he still recorded nine rushes for 43 yards and a rushing touchdown to go along with six receptions for 33 receiving yards.
Dallas Cowboys (second stint)
In March 2018, the Raiders traded Olawale and a 2018 sixth-round pick to the Dallas Cowboys for a fifth-round pick. On March 13, 2019, Olawale signed a three-year, $5.4 million contract extension with the Cowboys. In his career, Olawale has rushed for 206 yards, racked up 413 receiving yards, and scored 7 total touchdowns while in the NFL. As a special teams player, he made 48 tackles, including a forced fumble. He also has fielded 2 kicks as an up-man on kickoffs, and taken them a combined 15 yards. On March 10, 2020, Olawale's second-year option was exercised by the Cowboys.
