Oakley played soccer at the high school level in the United States with Mt. Saint Vernon.[1] In the 2012 season, he served as the team captain and helped the team win the National District title and was named to the second team all-region.[2] The following season, he made the transition to the college level by enrolling in the Louisburg College soccer program.[3] During his two-year tenure with the Hurricanes, he assisted the team in securing the Region X tournament.[4]
Early career
After the conclusion of his college stint, he played in the National Premier Soccer League with Myrtle Beach Mutiny.[5] In 2015, he went abroad to play in the Southern Ontario-based Canadian Soccer League with Burlington SC.[6] He primarily played in the league's second division with the reserve squad where he finished as the club's top goal scorer with 12 goals.[7] Oakley would also feature with the senior team where he recorded a hattrick against Scarborough SC.[6] His hat-trick would help the club secure a playoff berth by finishing sixth in the first division.[6] Burlington would be eliminated from the playoffs in the first round by the York Region Shooters.[8] The reserve team was also defeated in the first round by Brantford Galaxy's reserve squad.[9]
In the summer of 2017, he returned to his former club Burlington where he once again finished as the club's top goal scorer with 7 goals. He would help the club clinch a postseason in the second division.[10] Burlington ultimately reached the championship final against FC Ukraine United where he contributed a goal but lost the match.[11][12]
He returned to Canada to sign with expansion side Guelph United in the summer of 2021.[15] In his debut season, he helped the club win the league championship and was named the league's defender of the year.[16] In the 2022 season, he re-signed with the club and participated in the 2022 Canadian Championship where he played in the preliminary round against HFX Wanderers FC.[17][18][19] For the second consecutive season, he was named the league's top defender.[20] Oakley returned for his third term for the club in 2023.[20]
Ireland
In the early winter of 2024, he went abroad to sign with Athlone Town in the Irish second division.[21] He made his league debut on February 16, 2024, and recorded a goal against Wexford.[22] Oakley helped Athlone clinch a promotion playoff berth and were eliminated in the second round by Bray Wanderers.[23][24]
^Krebs, Oliver (12 February 2018). "Krähen brennen auf den Start" [Crows burn for the start]. extra-verlag.de (in German). Retrieved 26 September 2018.