[2] The coach for the North Winnipeg Nomads asked his mother if he could play football as they had an injured player and she allowed the request.

[2] As a senior at Oak Park, Oliveira was named the Winnipeg High School Football League (WHSFL) Potter Division Offensive Player of the Year after rushing 170 times for 2,220 yards and 34 touchdowns, and catching six passes for 142 yards and two additional touchdowns.

[11] Oliveira was named one of five finalists for the second annual Jon Cornish Trophy given to the most outstanding Canadian player in collegiate football.

[15] Oliveira injured his ankle during a Week 3 game against the Edmonton Eskimos while working on the kick return team which required surgery, and as a result he missed the rest of the 2019 CFL season.

[18] That year, he played and started in all 18 regular season games where he rushed for over 1,000 yards for the first time in his CFL career, while also scoring five total touchdowns.

However, prior to entering free agency, the Blue Bombers announced that he had signed a two-year contract extension with the team on February 6, 2024.

[19] Oliveira was a non-participant for training camp for the 2024 season due to a knee injury, but nonetheless played in the season-opening Grey Cup rematch against the Alouettes.

[21][22] He was inactive for the team's week 2 loss to the Ottawa Redblacks and was named the backup to Johnny Augustine for the Blue Bombers' next game against the BC Lions.

[21] However, after the Lions jumped to an early lead, Oliveira began receiving the majority of the snaps in the second quarter and finished the game with nine carries for 64 yards while the Bombers dropped to an 0–3 start to the year.

[2][3][29] His sister got a soccer scholarship to the University of Winnipeg where she studied criminal justice and later worked at the Manitoba Law Courts.

[2] Oliveira has been featured on multiple episodes of the YouTube channel The Dodo for his contribution of rescuing and fostering animals.