According to media reports, the 33-year-old has become the front-runner for the vacant manager's job at Stamford Bridge following his resignation from Porto after a single hugely successful season.
His short career - which spans just 20 months as head coach - and lack of Champions League experience means he is a gamble for Chelsea owner Roman Abramovich, for whom clinching Europe's top club trophy seems to have become an obsession.
None of the experienced coaches the Russian oligarch has employed since taking over the club in 2003 have won the trophy, including Mourinho, World Cup winner Luiz Felipe Scolari and twice European Cup champion Carlo Ancelotti, with the unlucky Avram Grant coming within one penalty kick of doing so.
Abramovich, whose efforts to bring Dutchman Guus Hiddink back to the club look to have stalled, may have been swayed to take a new approach by Villas Boas' precocious competence in leading Porto to a Europa League win last month.
The Russian has always wanted Chelsea to win with style, and Villas Boas's rampant Porto showed immense attacking flair to win the Portuguese League undefeated and thrash serious rivals like Spain's Villarreal in the Europa League.
The Portuguese has cited former England coach Bobby Robson, who gave him his first break at Porto as a keen 16-year-old, as a major influence in his passion for attacking football.
The pressure of pleasing demanding Premier League fans and media would hardly unnerve Villas-Boas, who worked as an assistant and scout for Mourinho at Porto, Chelsea and Inter Milan before going solo to save Academica Coimbra from relegation from the Portuguese Premier League in October 2009.
The three-year spell at Chelsea with Mourinho means Villas-Boas has insider knowledge of how the club and its owner operate.
His relationship with Abramovich would almost certainly define his success and Villas-Boas has already shown he can deal with a tough boss like Porto's Jorge Pinto da Costa.
With ample resources available, Villas-Boas would have to show he can produce results from an expensive transfer policy, especially after Ancelotti failed to transform a poor season with the pricey acquisition of Spaniard Fernando Torres.
When Mourinho joined Chelsea, he took two Porto players with him and media reports in Portugal suggest Villas-Boas could take prolific striker Radamel Falcao and midfielder Joao Moutinho to London.
A shrewd market operator - as the signing of Moutinho and promising Colombian winger James Rodriguez showed - Villas-Boas would also face the task of rejuvenating a squad that has been together for several years.
He showed leadership at Porto, with players praising his motivational skills and meticulous analysis of opponents, perfected during his days as observer and scout for Mourinho.
An ambitious coach who says he is also inspired by Barcelona's Pep Guardiola, the young Portuguese knows his ultimate test at Chelsea would be to lift the Champions League with the creative style perfected by the Catalan coach.
