Roma heating up pursuit of Oosterwolde with offer being prepared

AC Milan are pursuing a loan deal for Real Madrid forward Endrick in January after failing to secure him in the summer transfer window. Jose Mourinho blocked the move months ago despite Milan's interest, but the Italian club believe the situation will shift in the new year and the Brazilian will be allowed to leave temporarily. Roma are also competing for the player and have made initial contact, with plans to speak to Real Madrid during their Champions League fixture in the coming weeks. Milan feel they retain a significant advantage because of their strong relationship with Endrick's representatives at RocNation, whom they have worked with regularly since 2020. Members of RedBird, Milan's ownership structure, also work with the NBA, which similarly deals with RocNation—a connection the club believes could prove decisive in January. Milan needed attacking reinforcement over the summer despite Omari Hutchinson's arrival, with Ruben Amorim forced to work around injuries to key players including Alexis Saelemaekers. The forward's availability on loan follows the pattern of last season, when a similar arrangement was used. Milan view the January window as a real opportunity to land a player who can provide the attacking depth Amorim's side requires.

Roma and AC Milan have both set their sights on Endrick, the Brazilian forward seeking greater opportunities after limited playing time at his current club. The Milan side hold a slight advantage in the race to sign him, with the competition expected to intensify in the coming weeks. Castro and Soulé, both Roma players, marked special nights with their debuts for Argentina's national team. Castro struck the post during the match, while Soulé produced several noteworthy moments. The pair now await Argentina's fixture against Benin, which will also serve as Lionel Messi's farewell appearance with the national team. Back at Roma, Gasperini is preparing the squad for an upcoming match against Como at the Sinigaglia stadium. Fabregas, Como's manager, recently offered praise for the Roma coach. Gasperini has also turned his attention beyond the Como fixture, directing a message toward Gattuso.

Former Roma defender Vincent Candela has predicted that Roma will defeat Real Madrid in their upcoming Champions League match at the Olimpico in ten days' time. Speaking at the FIP Gold Mediolanum Padel Cup in Perugia, Candela said: "It will be a celebration. I think Roma will win. I don't say it as a fan, but because I look at the characteristics of Gasperini's squad and the comparison with Mourinho's." Mario Hermoso has established himself as a cornerstone of Gasperini's Roma, impressing with his adaptability to the coach's tactical system. The club is now preparing to open contract renewal talks with the Spanish defender. Hermoso is seeking a two-year extension that would take his contract to 2029, but Roma's policy for players over 30 typically involves annual renewals. Both sides have expressed a willingness to continue together, with negotiations expected in the coming weeks. Elsewhere, Roma's interest in Frosinone's Giorgi Kvernadze—a Georgian prospect born in 2003 who has impressed early in the season—has prompted Frosinone president Maurizio Stirpe to distance the player from the market. Stirpe told the Corriere della Sera: "The possible sale of Kvernadze? Today it's only talk, I haven't received any phone calls. I only ever wait for official and concrete proposals." No formal offers have been made for the right-footed winger, whom Gasperini is reportedly keen to add to his squad.

Gian Piero Gasperini is already planning Roma's January window despite the club sitting top of the table with a functioning attack led by Dybala and Malen. Between appearances at the Trento Festival and work at Trigoria, Roma are targeting reinforcements in the attacking department, focusing on players currently struggling for minutes at their clubs. A conversation between CEO Galantic and Gasperini at the festival underscores Roma's philosophy of planning winter moves in advance. Roma's priority remains a quality wide forward, with evaluation also ongoing into a more complete profile like Oosterwolde. Four players already tracked in the summer transfer window remain in the club's sights: Gittens, Leweling, Luiz Henrique and Endrick. The common thread linking them is a shortage of regular playing time. Gittens, a Gasperini favourite, has yet to debut in the Premier League. Leweling plays only sporadic minutes at Stuttgart and was excluded from the initial squad list under new national team coach Klopp. Luiz Henrique remains blocked in Russia by bureaucratic issues that have also cost him national team call-ups. Endrick's situation is the most delicate. Mourinho secured him at Real Madrid over the summer, but the Brazilian has virtually disappeared: just four minutes across La Liga and the Champions League combined. That picture of underuse could shift as soon as November, when UEFA will make decisions on the Settlement Agreement, opening new scenarios potentially favourable to Roma heading into the winter market.

Head coach Gian Piero Gasperini is pressing Roma to strengthen their attacking ranks in the January transfer window, a priority that remained unmet during the summer. At the Festival dello Sport in Trento, CEO John Galantic was asked about a possible January arrival and responded: "Nice question." Gasperini immediately added: "Very nice." While the comment was partly tongue-in-cheek, it underscores the coach's determination to add an attacking winger, a position he had already requested in the summer window. Roma's focus remains on securing an attacking wide player, though the club has also considered a full-back option in Jayden Oosterwolde. Four names dominate the shortlist: Jamie Gittens, Jamie Leweling, Luiz Henrique and Endrick. A common thread links most of them — they are struggling for minutes at their current clubs. Gittens, reportedly among Gasperini's preferred targets, has not yet made a Premier League appearance. Leweling has accumulated only 146 minutes across Bundesliga, German Cup and Champions League competition for Stuttgart without starting a match, a lack of game time that also cost him a place in Jürgen Klopp's initial squad list as Germany's new national team coach. Luiz Henrique remains in Russia following bureaucratic obstacles that delayed Roma's pursuit last summer; the Brazilian has also lost ground in the national team setup, making a January reopening of talks less straightforward. Endrick represents a different scenario. The Brazilian was close to Roma in the summer before José Mourinho chose to retain him at Real Madrid. The Portuguese manager had praised him publicly, but has given him only four minutes across league and Champions League fixtures so far. Should his situation remain unchanged, a loan move could become realistic in January. Financial constraints will prove decisive. UEFA's ruling on Roma's Settlement Agreement breach is due in November, and that verdict may constrain the club's negotiating room. Gasperini's technical priority is unmistakable — an attacking wide player — but the scope for converting that request into a concrete deal remains to be determined by the financial outlook.

Roma remain fixed on an attacking winger for the January transfer window, with four candidates dominating discussion at Trigoria: Leweling, Gittens, Luiz Henrique and Endrick. Head coach Gasperini is methodical in his approach—this is his familiar pattern, reshaping the squad when the window reopens. The club also has a full-back slot in mind, though a potential return to Oosterwolde cannot be ruled out. The winger target, however, commands the focus of sporting director D'Amico and Roma's recruitment team. Each of the four front-runners faces obstacles at their current clubs. Gittens, reportedly Gasperini's preference, has yet to debut in the Premier League and suffered an injury while on U21 duty. Leweling has accumulated only 146 minutes of action and missed selection in the new national team coach Klopp's initial squad of 44 players during a difficult phase at his club. Luiz Henrique remained in Russia due to bureaucratic issues and lost his international call-up, making a January move appear unlikely. Endrick, protected and blocked by Mourinho in summer, has been sidelined at Real Madrid with just four minutes of playing time granted. Much hinges on November, when UEFA will rule on Roma's alleged breach of the Settlement Agreement. The expectation is that a loan deal with a purchase option—a formula rejected by the club in summer—may now gain traction and suit Gasperini's requirements.