Tottenham will exit the Europa League after losing Basel on penalties in the second leg of the quarter final, with Clint Dempsey and Michael Dawson both putting in top-class performances for the north London side in the thrilling tie.
Basel began the game on the defence, with Tottenham dominating possession and looking to start well. And a massive mistake by Dragovic resulted in a goal for their efforts, as the centre-half attempted to intercept a pass from Jan Vertonghen but went to ground on the slippery surface instead, leaving the ball to Clint Dempsey, who nipped it past keeper Yann Sommer.
But Spurs weren't given much time to celebrate, with Basel responding quickly and piling the pressure on Villas-Boas' men. And just four minutes later, with Mohamed Saleh found the bottom corner of the net as the result of a brilliant counter attack.
The 1-1 scoreline had Tottenham heading home on away goals, and the side looked to have no answer for Saleh as he kept pushing the side for the remainder of the first half.
And just four minutes into the second half, Basel struck again, thanks to the man who put them a goal down in the first place; Dragovic took the rebound from Brad Friedel, who couldn't get his hands around Fabian Schar's header, to score from close range.
Spurs desperately needed a goal now to send the game to extra time, and their lack of attacking options without Gareth Bale and Aaron Lennon were clearly hurting them.
Villas-Boas juggled the team as best he could, bringing on youngster Tom Carroll, Tom Huddlestone and Benoit Assou-Ekotto, and it seemed to do the trick as Dempsey found the back of the net in the 82nd minute. Partly the doing of the Basel keeper, Demspey was able to control a long-range free kick and fired the ball beyond Sommer's grasp.
The goal seemed to fire up the team, with Kyle Walker coming close to scoring just minutes later, but their good run wouldn't continue, with Vertonghen receiving a red card for an ill-timed tackle on Basel captain Marco Streller as he ran towards goal.
The ending 1-1 result meant that the sides would go into extra time, and Huddlestone moved into the back to fill in for Vertonghen, as Villas-Boas toyed with the idea of playing for penalties. Adebayor continued to suffer from poor finishing, resulting in continual loss of possession for Tottenham, and Basel kept creating chances, with Mohamed Elneny and Marcelo Diaz both coming dangerously close to scoring.
Dawson was particularly outstanding for Spurs over the extra time as his teammates tired, clearing the line on more than one occasion for the side. And as a result of their defensive efforts, the game finished with the same result as the regular 90 minutes produced, and both teams prepared for penalties.
Tottenham don't have a great track record with penalties, having lost their last six in a row, and the side looked to repeat such a defeat once more as Tom Huddlestone had his first penalty saved and Basel scored their first two. Gylfi Sigurdsson was able to save Spurs' blushes with the second penalty, powering the ball directly into the middle of the net, but after Fabian Frei made it 3-1 for Basel, Adebayor once again was disappointing in front of the net, missing to essentially gift the Swiss side victory. Marcelo Diaz's successful penalty was the final nail in the coffin, and Basel will move through to the semi final.