Having barely featured for the Blues during pre-season, it came as little surprise when Chilwell was made available by new head coach Enzo Maresca.
However, an exit from Stamford Bridge failed to materialise, leaving the England international facing the prospect of four months without football.
Maresca reacted by reintegrating the 27-year-old back into the senior setup, the left-back earning 45 minutes against Barrow in the EFL Cup third round last month.
Nevertheless, the Italian later doubled-down over his decision to leave Chilwell out of his squad for the Conference League, a further sign that the player's days in West London were numbered.
What next for Chilwell?
Unless Chelsea suffer injuries to several of their left-back options, there is little prospect of Chilwell making an appearance in the Premier League before the turn of the year.
Marc Cucurella, Renato Veiga and Malo Gusto are all regarded as ahead of him in the pecking order, leaving the former Leicester City man to hope for interest in January.
According to TEAMtalk, Chilwell is one of several players who have been identified as a potential addition by Borussia Dortmund.
The Bundesliga giants allegedly turned down the chance to sign Chilwell during the summer, but they are seemingly prepared to reconsider their stance.
Dortmund are said to be contemplating a move for Bournemouth's Milos Kerkez, although that may prove more costly with the Cherries expected to demand big money for the younger Hungary international.
Dortmund to take similar route as earlier this year?
In this year's January window, Dortmund negotiated terms for then-Chelsea player Ian Maatsen to make the temporary switch to the Westfalenstadion.
That proved to be an inspired piece of business, Maatsen starring for Dortmund on their run to the Champions League final before they lost to Real Madrid.
While they would ultimately miss out on the permanent addition of the Dutchman, they struck up a positive relationship with their Chelsea counterparts and could make use of it yet again.
Chelsea co-owners Todd Boehly and Clearlake Capital are likely to be open to both permanent and loan bids for Chilwell as they bid to reduce their wage bill.