Ola signed for the club as an Under-11 and started his career as a right-winger before establishing himself as a highly mobile full-back, who is also capable of playing as a central defender. He made his youth team debut as a schoolboy in the 2012/13 season and went on to start in both legs of the semi-final and final of the FA Youth Cup.
In his debut season as a scholar, Aina featured regularly for Adi Viveash’s Under-18s and was an ever-present on the way to Youth Cup success. European Under-19 and domestic Under-21 debuts followed, with the defender utilised as a centre-back as the senior age group won their domestic title.
Aina’s prominence in the Youth Cup continued in 2014/15 when he won the trophy for the second time. His run of 18 consecutive appearances in the competition across three seasons is unprecedented. He also played in every game in the Under-19s’ triumphant UEFA Youth League campaign, scoring in the group opener at home to Schalke, while establishing himself as an Under-21 regular. Aina signed a first-year professional contract in October 2013 committing him to the club until the end of the 2015/16 season. Currently, he is looking at the footsteps of the likes of Ruben Loftus-Cheek into the first team.