When Chelsea travel to Naples for the first leg of their Champions League knockout stage match, it will be the most important match for the Blues in their new manager's reign this season.
The match will not only test the squad's quality and resilience but could also turn out to be Villas-Boas' fate decider. The Mourinho-repeat has been in troubled waters since taking charge at the start of this season.
With his team fighting for a top four finish (leave aside any title race), out of the League Cup, struggling in the FA Cup and suffering reported player discontent along with his failed tactics and decisions, the season can only get better for the 34-year-old Portuguese.
The Champions League is the most cherished trophy at Stamford Bridge, and Villas-Boas will be looking to resurrect his failing reign with a boost.
A win against Napoli, much tougher than it may actually sound, could help Villas-Boas gain back the fans who seem to be losing their patience with their disoriented manager. The win could also help him calm Chelsea owner Roman Abramovich's slowly unnerving patience, aside from helping his squad regain confidence.
Chelsea's trip to Napoli can best be described as their Italian Job, which is their most important fixture this season. A mistake there, and the season could end up in tatters, which would undoubtedly see them end another season with a barren trophy cabinet.
Moreover, that could see Villas-Boas leave Chelsea even before than the older players who are scheduled to be sold this summer.
In the following slides we take a look into the eight players to watch in Chelsea's most important fixture of the season when they face Napoli on Tuesday.