Much of the attention will be on Mourinho and his opposite number as Villas-Boas is not only a former Chelsea manager, but also worked with his fellow Portuguese at Porto, Stamford Bridge and Inter Milan.
It will be the first time the pair have encountered each other in opposing dugouts after their relationship broke down in 2009.
If events on the touchline provide intrigue, so too will the team sheet submitted by Mourinho, who rather disingenuously suggested Tuesday night's Capital One Cup encounter at Swindon was a chance for fringe players to win a first-team place.
Mourinho has admitted he is uncertain of his best team, but whether Juan Mata has done enough to earn a place in the starting XI at White Hart Lane remains to be seen.
It is likely the Portuguese will field what he considers to be his best side against a Spurs squad he believes are one of five teams who could challenge the Blues for the Barclays Premier League title.
Fernando Torres, who scored one and made another at the County Ground to set up a fourth-round tie at Arsenal, could continue at striker, ahead of Samuel Eto'o and Demba Ba.
Gary Cahill is likely to remain at the heart of the defence, a position he has played in seven of Chelsea's eight matches this term; the only one he did not start was the loss at Everton.
Following successive losses at Goodison Park and to Basle in the Champions League, Cahill believes Chelsea have bounced back strongly.
"It was a tough week, especially when we lost back to back," Cahill told Chelsea TV.
Source: PA
Source: PA