The 35-year-old, whose side have won eight of their nine games this season, worked under his compatriot for several years, and takes on the club he was sacked by in March 2012Tottenham go in search of just their fourth Premier League win over Chelsea when they host their London rivals on Saturday.
The White Hart Lane club have a wretched record against their Stamford Bridge counterparts, having posted only three wins in their 42 previous meetings since the division's inception in 1992.
They have failed to beat Chelsea in their last six top-flight encounters, with their last victory coming courtesy of goals from Jermain Defoe and Gareth Bale in a 2-1 home success in April 2010.
However, Tottenham boss Andre Villas-Boas can feel confident of ending that sequence against the club he managed between June 2011 and March 2012.
His side have picked up four wins from their first five Premier League games this season and sit joint top with arch-rivals Arsenal.
|MASTER VERSUS PUPIL AT WHITE HART LANE
|66/1||Chelsea are 66/1 with bet365 to beat Tottenham 4-2
However, Villas-Boas - who also worked under Jose Mourinho at Chelsea during his compatriot’s first spell at Stamford Bridge between 2004 and 2007 - has played down talk of a title challenge.
"What is happening to us now puts us in a positive mood ... but it can change very, very quickly," said the Portuguese.
"At the moment we are on a good run, but there are no clubs on maximum points and this year will be very tight at the top."
Villas-Boas has an almost fully-fit squad to choose from for the visit of his former mentor, with only Etienne Capoue (knee) and Younes Kaboul (thigh) definitely unavailable. Full-back Danny Rose (ankle) is expected to return.
Chelsea, meanwhile, go into the clash having collected just one point from their two away Premier League matches this season, after drawing 0-0 at Manchester United and losing 1-0 at Everton.
However, in keeping with their incredible record against Tottenham, they ran out 4-2 winners in the corresponding fixture last season.
Juan Mata was the architect of that victory, scoring two goals and claiming an assist, but the Spanish playmaker appears unlikely to start this time around after falling out of favour since Mourinho’s return.
The former Real Madrid boss also has a largely fit squad available, but he will definitely be without Marco van Ginkel after the Dutchman suffered a cruciate knee ligament injury in the League Cup win at Swindon Town on Tuesday that will rule him out for at least six months. Brazilian midfielder Ramires (hip) is also a doubt.