AS Roma has agreed to a loan deal with Fenerbahçe for the transfer of Oosterwolde, with an option to buy for €18 million. The deal is a loan agreement with an option to buy, which can become a mandatory buyout under certain conditions. Oosterwolde currently has a contract with Fenerbahçe until mid-2028, but AS Roma wants to sign him for five seasons.

Gian-Piero Gasperini believes that Oosterwolde fits perfectly in his system, which could be beneficial for the Italian club. AS Roma has already secured a spot in the Champions League, while Fenerbahçe still needs to play against Olympique Lyon. Oosterwolde received his training at FC Twente and has previously been linked to Parma, who offered €3.3 million for him.

AS Roma begins their new Serie A season on Monday against Fiorentina, but it seems unlikely that Oosterwolde will be involved in that match, as he will likely join AS Roma after the completion of Fenerbahçe's Champions League tie against Olympique Lyon.