Villas-Boas said: "It's very disappointing because they've played like heroes. In penalties anything can happen but I think we have set a standard for English football for the way we approached this competition.
"We had assigned the strongest penalty takers and practised them but the nature of them is very difficult and you can never recreate the same stress in a game.
Villas-Boas was only six years old the last time Spurs competed in a European semi-final, with the heroes of 1984 including the likes of Steve Perryman, Graham Roberts and Steve Archibald.
But following in the footsteps of those esteemed players was always going to prove his most substantial test yet after preparing for this second leg without Bale, Jermain Defoe and Aaron Lennon.
The absence of Bale, in particular, left Spurs devoid of pace and an attacking threat but with the Wales international missing, the onus was on Spurs to kill off those persistent "one-man team" theories in such a high-pressure game. Sadly, it was only Dawson, Kyle Walker and substitute Tom Huddlestone who escaped with any real credit.
Backed by 1,800 travelling fans, Spurs escaped two early scares when Fabian Schar's free kick drifted narrowly wide before Mohamed Salah – guilty of missing so many chances at White Hart Lane – added another to his collection with a volley over the crossbar.
But Spurs were energetic in midfield and comfortable in possession and stunned the boisterous home support by taking the lead with their first chance on 23 minutes.
Vertonghen's forward pass should have been easily cut out by Aleksandar Dragovic but the centre-half slipped on the greasy turf to free Dempsey, who rounded Yann Sommer before rolling the ball into the empty net. It was the first goal Basle had conceded at St Jakob-Park since early October.
Thoughts of a possible semi-final lasted only four minutes. Mousa Dembele's pass was intercepted and Marco Streller sent Salah clear, with the Egyptian poking a low shot into the bottom corner.
Spurs were rattled, in front of David Platt, who had been dispatched by Roberto Mancini to carry out a spying mission ahead of next Sunday's game against Manchester City.
Adebayor was having one of those teeth-gnashingly frustrating evenings, albeit in a difficult lone forward role, while Kyle Naughton was frequently exposed on the left side of defence.
And Basle seized a crucial lead on the night four minutes into the second period as the visiting defence once again fatally hesitated.
Flares lit up in the noisy end behind Friedel's goal and suddenly the alarm bells were ringing even louder for Spurs.
The sheer lack of options available to Villas-Boas were laid bare before the hour as young midfielder Tom Carroll was introduced for Dembele, who was clearly struggling.
Spurs only needed one goal to force extra time and Basle's careless passing presented them with hope. And it was Dempsey who provided yet another dramatic comeback, poking home at the far post after he was found by Huddlestone's raking pass.
Spurs did suffer a damaging end to normal time when Vertonghen was given a straight red card by referee Olegario Benquerenca for scything down Streller.
Huddlestone was forced into a central defensive role in his place but excelled in extra time, constantly reading the danger raining in from Basle's flanks and clearing the danger.
Penalties were obvious, as fatigue kicked in. Schar and Streller scored either side of Huddlestone's effort that was saved, and while Gylfi Sigurdsson did manage to hit the target, Fabian Frei and Diaz punished Adebayor's woeful kick to seal the tie.
Spurs have not won a penalty shoot-out since January 1994, when they beat Peterborough in an FA Cup 3rd round replay. It was a bitter end to a stirring campaign.
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