The 38-year-old midfielder, currently at New York City, confirmed on Sunday that he will hang up his boots at the end of the current Major League Soccer season.
Pirlo played under Antonio Conte, now Chelsea boss, at both Juventus and the Italy national team during a superb playing career in which he won six Serie A titles, two Champions Leagues and a World Cup.
When asked about a possible reunion with Conte at Stamford Bridge, the Italian midfielder remained coy.
"My future, I don't know yet. I will return to Italy in December," he told 'Gazzetta dello Sport'.
"An assistant to Conte? People are saying that. I have my ideas but I need time to decide."
Pirlo has been in New York for the past three campaigns but has played in just 15 of the club's 32 games this season.