Roma monitoring Oosterwolde as deadline approaches

Jamie Gittens has struggled to replicate his Borussia Dortmund form since joining Chelsea in summer 2025 for more than €50 million. The English winger, who arrived at Dortmund from Manchester City's academy in 2020 at age 16, had emerged as one of Europe's most exciting attacking prospects during the 2024–25 season, scoring 12 goals and providing three assists while leading the Bundesliga with an average of 4.2 successful dribbles per match—well ahead of rivals Jamie Leweling, Michael Olise and Kingsley Coman. He also ranked second across Europe's top five leagues for successful dribbles that season with 76, behind only Lamine Yamal. At Chelsea, however, Gittens has managed only 29 appearances, two goals and six assists, hampered by muscular injuries and rotation policy despite the arrival of manager Xabi Alonso. The 2004-born winger's career at Dortmund was marked by repeated setbacks—a serious ankle ligament injury early in his development and a shoulder injury interrupted his progress before his breakthrough in the 2023–24 Champions League season. Gittens scored in a crucial match against AC Milan at San Siro that helped Dortmund reach the knockout stages. His 2024–25 campaign under Nuri Sahin and then Nico Kovac saw him finally deliver on his enormous potential with clinical finishing and elite dribbling. The article suggests Gian Piero Gasperini and Roma could provide the right environment for him to rediscover that form and reignite his trajectory.

Roma have been offered Oosterwolde, the Fenerbahçe defender who can also operate as a left-back, as the club continues to search for reinforcements with eleven days remaining in the transfer window. The Dutch defender has long been on Roma's radar, but his current status is a concern: he is out with a muscle problem, and Roma will conduct fitness evaluations before making any move. Any deal for Oosterwolde would have to be structured as a loan, matching Roma's approach to other potential signings. Luis Henrique is also being pursued on a temporary basis, though negotiations with Inter remain difficult—the Nerazzurri want to include a €28 million obligation in the agreement, creating distance between the clubs. Moves for Cacciamani and Udogie are considered unlikely.

Roma have made direct contact with Chelsea over Jamie Bynoe-Gittens, an English winger currently out of favour at Stamford Bridge and on the radar of head coach Gian Piero Gasperini. The move remains complicated by differing terms: Chelsea are pushing for a permanent sale because of restrictions on outgoing loan slots, while Roma want to bring him in on loan only. According to Riccardo Trevisani, the deal could only reopen if Chelsea soften their conditions. Bynoe-Gittens, who recently spent time on loan at Borussia Dortmund, fits Gasperini's style of play and represents a low-cost option. His wages align with Roma's wage structure, a factor that appeals to the club's ownership as they seek to add depth without heavy investment. The operation differs from other targets like Fofana, whose transfer has stalled over cost concerns. The player remains on Roma's shortlist as the club's transfer team, led by Tony D'Amico, searches for the right formula and timing in the closing days of the window. No advanced talks are currently underway, but Bynoe-Gittens's profile matches Roma's requirement for two new attacking reinforcements to support Gasperini's squad.