The England full-back was establishing himself as a key player under Mauricio Pochettino and even took the captain’s armband in the absence of Reece James.
Another hamstring, however, has derailed the 26-year-old’s season and he is not expected back before December.
Chilwell limped off at the end of Chelsea’s 1-0 Carabao Cup win over Brighton earlier this month and there are concerns given the number of hamstring injuries the defender has suffered during his time at the club.
His absence adds to Mauricio Pochettino’s injury crisis at Stamford Bridge, with the likes of Reece James, Romeo Lavia, Christopher Nkunku, Wesley Fofana and Benoit Badiashile also ruled out.
Taking to Instagram, Chilwell sent a message to the club’s supporters.
“Can’t catch a break,” he wrote.
“Believe me, I am more frustrated than you guys. All I can do now is help the team as best as I can from the sidelines, until I can get back to giving everything for the club on the pitch again.
“Ups and downs but that’s life. Just focused on getting this club back where it deserves to be. Thank you as always for the love, Chels fans.”