The Blues have spent millions of pounds on their academy but captain John Terry remains the last player to become a first-team regular after coming through the ranks.
That was more than a decade ago, with the arrival of Roman Abramovich's billions allowing the club to hoover up the world's best ready-made talent.
That has arguably led to limited chances for youngsters to force their way into the side, something that could soon be about to change, according to Chelsea's current manager.
Villas-Boas said: "They are coming. They are coming. There's a generation coming. I think so. I believe so."
Chelsea's youth team have certainly progressed in recent years, winning the FA Youth Cup in 2010 for the first time since 1961.
They were also runners-up two years earlier and were semi-finalists last season.
However, the star of their cup-winning side, Josh McEachran, has made only a handful of first-team appearances and has seen his game time extremely limited under Villas-Boas.
The 18-year-old was sent out on loan to Swansea this week and Villas-Boas backed him to return readier to challenge for a place.
He said. "It's fair to say that with his playing time, we will have another vision of his talent coming through within the Premier League."
Villas-Boas wants all his loan players to flourish at the clubs they have been sent to, telling them it is not good enough for them to return to Stamford Bridge having failed to establish themselves elsewhere.
As well as McEachran, Patrick van Aanholt and Gael Kakuta were farmed out again this week, moving to Vitesse Arnhem and Dijon, respectively.
The latter two are at their second loan clubs this season, having made just a handful of appearances each at Wigan and Bolton.
Villas-Boas said: "If they're unable to triumph over there, it can't just be a manager's decision.
"They have to show they are capable of triumphing in a difficult environment.
"It is never a good option if you come back early - it means something went wrong."
Villas-Boas claimed the only way to ensure a conveyor belt of young talent for the first team was to revolutionise the structure of English football.
Calling for Chelsea to be allowed to field a B team in the npower Championship, Villas-Boas said: "The youth development system in England is not right.
"The reserve team league is not competitive. The youth levels are not competitive enough.
"In my opinion, there is a missed link between age groups in all competitions.
"They should be national championships played between teams from around the country. The older ones should play nationally. The younger ones should play regionally.
"It is that which generates talent."
Meanwhile, the group of fans who hold the key to Chelsea's hopes of moving to a new stadium meet on Friday for the first time since rejecting the club's bid to buy back the freehold of Stamford Bridge.
Chelsea Pitch Owners, who in October voted against selling the land beneath the Blues' current home to Abramovich, will hold their annual general meeting on Friday morning.