AS Roma is looking for a player who can fit into their 3-4-2-1 system, and Oosterwolde's versatility could be an asset. The 25-year-old Dutch player has experience playing as a full-back, and his defensive skills could be valuable to the Italian club. Oosterwolde has played for FC Twente's youth academy and has experience playing in Turkey with Fenerbahçe, where he has made 112 appearances since joining in 2023.
AS Roma's coach, Gian-Piero Gasperini, may see Oosterwolde as a suitable fit for the team. The Italian club previously tried to sign Givairo Read from Feyenoord, but the deal fell through due to Feyenoord's high asking price. If the transfer goes through, Oosterwolde would sign a five-year contract with AS Roma.