For the last four seasons, Spurs prospered under the reign of Harry Redknapp, who took over a side that had just finished 11th in the league and transformed them into one that finished in the top five in the last three campaigns.
Yet, in a move many still find difficult to understand, the north-London outfit decided to part ways with the fan favourite at the end of last season, after both sides reportedly failed to agree terms on a new contract.
The fact he was subsequently replaced by a man who lasted less than nine months in charge of Chelsea last term raised even more eyebrows, but is Villas-Boas already destined for another doomed spell in English football's top flight?
One swallow doesn't make a summer
It is true that Villas-Boas didn't have the best of times in charge of the Blues. When he was finally relieved of his duties in March, Chelsea were fifth in the league, out of the Carling Cup and staring elimination from the Champions League round-of-16 in the eye. The fact that his replacement, Roberto Di Matteo, went on to lead the side to triumphs in the FA Cup and Champions League did nothing to help his case.
Nonetheless, that spell doesn't take away the fact that he's still one of Europe's most-intelligent young tacticians and at 34, still has plenty of time for development. Patience was the one thing that Blues owner Roman Abramovich failed to offer the Portuguese, but if Spurs do, this could be the start of another glorious chapter in the club's history.
Villas-Boas did learn his trade under Sir Bobby Robson and Jose Mourinho, two of the most famous managers in the history of football, and many often forget he was only 33 when he led Porto to the treble of the Primeira Liga, Taca de Portugal and Europa League.
When Chelsea originally named him as Carlo Ancelotti's replacement last summer, they did call him "the outstanding candidate for the job" and "one of the most talented young managers in football" who had "the ambition, drive and determination" to match that of the club.
The lack of player power at White Hart Lane
The one thing that could make the difference and see Villas-Boas succeed at Tottenham is the plain fact that none of his key players are in the same age bracket as him; simple as that.
At Stamford Bridge, it was no secret that John Terry, Frank Lampard and Didier Drogba led the dressing room and considering they were all around the same age as their then-boss, it was easy to see why they would question taking orders from someone with no experience as a professional footballer.
Apart from goalkeepers Brad Friedel and Carlo Cudicini, there is no player in the Spurs squad that is remotely close to being as old as their new boss, and that bodes well for their prospects. Add to that the fact that even the longest-serving players weren't always automatic starters under Redknapp and you get a playing list that's devoid of any gigantic egos.
Do Spurs have enough in reserve?
The one problem that Tottenham encountered last season, as pointed out by several pundits, was that they had a formidable starting XI that could match any team in the league, but a bench lacking in depth exposed them when injuries and suspensions hit.
As much as he is a talented prospect that could one day play for England, bringing on Jake Livermore for Scott Parker didn't quite strike the same fear in the hearts of their opponents.
Already this summer, Spurs have made two new signings in Jan Vertonghen and Gylfi Sigurdsson, with more to come perhaps, as Villas-Boas has already hinted he is on the lookout for a new striker.
Vertonghen will be a more-than-capable replacement for former captain Ledley King, but considering the ex-England international was hardly a regular in recent seasons due to injuries, it means that Villas-Boas will have four accomplished centre-backs to pick from, including Younes Kaboul, Michael Dawson and William Gallas.
Likewise, Sigurdsson will offer a different option in the middle of the park and will fit in perfectly playing as the link-up between anchorman Scott Parker and playmaker Luka Modric. Should the Iceland international manage to repeat the form he showed whilst on loan at Swansea earlier in the year, he may easily force his way into Villas-Boas' starting XI.
Modric, Bale still key to Tottenham's fortunes
Nonetheless, there is no denying the first two names that will be on Villas-Boas' starting XI when Tottenham get their campaign underway against Newcastle on August 18 will be that of Luka Modric and Gareth Bale.
The latter committed his future to the club earlier in the summer by putting pen to paper to a new four-year deal, and based on his stunning displays over the past two seasons, the Wales international could easily go on to become the world's best player, especially given he's still only 23.
Bale spent much of last season being linked with a move to Barcelona, and while many more offers are bound to be tabled from now till 2016, Villas-Boas will be thankful he begins his reign with arguably the world's best left-winger at his disposal.
The situation with Modric is less certain, although it now appears as though Real Madrid are the only club in for him, unlike last summer when both Chelsea and Manchester United were desperate for his services.
Parker may be the one who spurs Tottenham on when the chips are down, but the Croatian playmaker is who combines all the separate components into a working machine with his vision, tactical nous and passing ability.
It won't exactly be the end of the world if Modric does depart from White Hart Lane before August 31, especially if Spurs do receive the £30million they are reportedly demanding from Real. Rafael van der Vaart, who has spent most of his Tottenham career playing out wide or in attack, is capable of taking over the playmaking duties, while Sigurdsson could also relish the chance of stepping up to the plate.
Still, if Modric does commit to the club, like Bale did a couple of months earlier, it would hugely boost their bid for a top-four finish.
When Villas-Boas took over at Chelsea last summer, he was identified as the man who could lead Chelsea to Champions League glory. He failed to do so, and just months after he was relieved of his duties, his replacement Di Matteo did just that.
Once again, the Portuguese has been handed a Europe-oriented target, although this time, qualifying for next season's edition will suffice for the Tottenham hierarchy.
Barring another victory by a Premier League club in the Champions League this season, it means that finishing in the top four will be Villas-Boas' goal for his maiden year in charge at White Hart Lane.
Manchester City, Manchester United and Chelsea are likely to claim the first three spots, leaving Spurs to battle it out for fourth spot with Arsenal, Liverpool and Newcastle.
Given the pre-season reinforcements he has been handed, and should he be able to convince Modric to stay for another term at least, Villas-Boas could survive in London far longer than he did the last time around.