Villas-Boas worked under Mourinho at Chelsea and Inter Milan before focusing on his own managerial career, which has now seen him sacked by Chelsea and Spurs.
Spurs replaced Villas-Boas with Sherwood, who is without managerial experience, much the same way in which Mourinho was succeeded by Avram Grant when his first spell ended in September 2007 and his fellow Portuguese by Roberto Di Matteo in March 2012.
Grant led Chelsea to the 2008 Champions League final and Di Matteo went one better after taking over from Villas-Boas, lifting the European Cup.
Mourinho declined the opportunity to appraise Sherwood, though.
"That is not my problem," Mourinho said. "My only problem is to feel sorry that one manager lost his job a couple of days before Christmas where he was completely enthusiastic about going forward with his contract at Tottenham.
"That is my only concern and my thoughts are only going to Andre and the other four guys who lost their jobs.
"Who they appoint, if it is permanent or not permanent, if he is experienced or not experienced, to me, to be fair, is not a problem."