AS Roma are considering another attempt to sign Chelsea winger Jamie Gittens as they prepare for the January transfer window, with manager Gian Piero Gasperini seeking greater depth and quality in attack.

According to FootballTransfers on Thursday, November 5, 2026, the Serie A side are ready to revisit their interest in the 22-year-old after identifying a lack of squad depth as a significant weakness.

Roma’s defeats against Manchester United and Real Madrid exposed their difficulty maintaining performance levels throughout demanding matches. At Old Trafford, they surrendered a two-goal advantage before losing 3-2. They had also thrown away a 3-1 lead in a 4-3 defeat to Real Madrid. Those collapses have raised concerns about the team’s ability to manage games and sustain intensity, increasing the pressure on the club to strengthen in January.

Gasperini had wanted to add a wide attacker during the summer transfer window but was unable to secure his preferred targets. Gittens remains among the options being considered as Roma reassess their recruitment plans. The club are also reportedly monitoring Real Madrid forward Endrick and Stuttgart winger Jamie Leweling, while Frosinone attacker Giorgi Kvernadze is another name under consideration.

A possible move for Gittens could be more realistic than it appeared previously because of his difficult start at Chelsea. The winger has struggled to earn regular opportunities under manager Xabi Alonso and was reportedly left as an unused substitute in five consecutive matches earlier in the campaign.

His progress has also been interrupted by an ankle injury that has kept him out of action since October. Before that setback, his appearances under Alonso were limited to the Carabao Cup, where he failed to record a goal or assist. The lack of regular involvement has raised questions about his immediate role in Chelsea’s plans.

FootballTransfers has also reported a considerable decline in his estimated transfer value. His valuation has dropped from €74.6 million to €34.5 million, reflecting the difficulties he has experienced since joining the London club. The figure is an estimate rather than a confirmed asking price, but it illustrates the change in his market assessment.

Roma have maintained their interest despite his limited impact at Stamford Bridge. The Italian club made several attempts to recruit him during the previous summer window, but Chelsea were unwilling to sanction his departure after only one season. The situation may now be different if his opportunities remain restricted and the club considers its options.

For Gasperini, adding another winger would provide more alternatives across the attacking positions and help Roma cope with the demands of competing in multiple competitions. Gittens could offer a chance to strengthen the squad while giving the player an opportunity to regain momentum through more consistent playing time.

No agreement has been reached, and Chelsea’s position remains uncertain. However, Roma’s renewed interest, combined with Gittens’ injury absence and limited opportunities, could make January an important moment in determining his future. A move to Italy may offer a fresh start, provided the clubs can agree on suitable terms.