Chiesa was heavily linked with a transfer from Liverpool during the summer, but a deal never materialized, leaving him to compete for playing time under manager Arne Slot.
Although he scored in Liverpool's 4-2 opening-day win over Bournemouth, his exclusion from the Champions League squad and absence from the bench in the Merseyside derby show that he is struggling to gain prominence.
Those close to Chiesa say he has remained professional despite the challenges, but patience will be tested, and January could be a crucial window for him.
Several Italian clubs, including Napoli, Atalanta, Roma, Milan, and Inter, have been monitoring Chiesa, while Atletico Madrid and Besiktas have also been linked to him.
In the Premier League, Fulham and Newcastle have also explored the possibility of signing him.
For now, Chiesa remains committed to Liverpool, but those close to him acknowledge that the next step will be delicate.
Chiesa doesn't want to settle for being the top player at a club that lacks ambition, but he must also consider whether there is a long-term place for him in Slot's plans.
The match against Southampton is significant for Chiesa, as it presents an opportunity for him to gain playing time and potentially reignite his Liverpool career.
A poor performance, on the other hand, could lead to more clubs exploring the possibility of signing him.