FC Twente
Oosterwijk came to FC Twente as a youth player. The attacker attended the FC Twente Football Academy and made his debut in professional football with Jong FC Twente in the Jupiler League in 2013. A year later, Oosterwijk played his first game in the main squad of the club, during the game with Vitesse he came on as a substitute. In the 2016/2017 season, Oosterwijk played on a rental basis for NAC Breda. Oosterwijk played 57 league matches for FC Twente in which he scored thirteen times.