On 13 September 2015, it was announced that Oliveira would be moving up to the Moto2 class for the 2016 season, with Leopard Racing. He was joined in the team by his Moto3 championship rival Danny Kent. Oliveira achieved three Top 10 results with a 9th place in Le Mans, 8th place in Catalunya and another 9th place in Brno, before breaking his collarbone after a collision with Franco Morbidelli during practice for the Aragon Grand Prix. Morbidelli was later penalized for the crash with Oliveira missing out on the race. He returned for the Japanese Grand Prix and was initially declared fit by the medical team, but eventually did not start the race after assessing his condition during free practice. In consultation with the team it was later decided that Oliveira would also not start in the following races at Phillip Island and Sepang, where he was replaced by Alessandro Nocco. Before the Aragon crash Oliveira had been comfortably leading the standings for Rookie of the Year throughout the season and he was behind by only one point after missing four races and returning for the final race of the year in Valencia. He finished the race in a commendable 13th place, but fell short of clinching the trophy by a single point with eventual Rookie of the Year Xavi Vierge finishing just ahead of him in 12th place.