Tottenham's rollercoaster ride in the Europa League came to a dramatic end as they suffered penalty shoot-out heartbreak in Basel.
Clint Dempsey put Spurs ahead, before Mohamed Salah and Aleksandr Dragovic scored to put Basel on course for victory.
Dempsey took the tie to extra-time with just eight minutes of normal time remaining - but Tottenham's task was then made much harder by the injury-time dismissal of Jan Vertonghen.
Basel threw everything at the Londoners in extra-time, but they could not find a way through and the game went to penalties.
Tottenham had not won a penalty shoot-out since 1994 - and it showed.
Tom Huddlestone and Emmanuel Adebayor both missed from the spot while Basel converted all four of their efforts to send Andre Villas-Boas' team crashing out of the competition.
Despite their hard work tonight on a ground where Bayern Munich and Manchester United were defeated last year, a dramatic run that has included red cards, an off the pitch stabbing, racist chanting, and two last-gasp wins, has now ended.
Villas-Boas can be proud of his squad's endeavours - but they would have not been in this situation tonight had they wilted so pitifully in last week's first leg.
It also remains to be seen whether the Portuguese's policy of playing his best players in the search of his second European trophy in three seasons has been a wise one with Tottenham's patched-up squad currently faltering in the home straight in the league.
The hosts were much more effective on the attack in the sold-out stadium on the banks of the Rhine.
Brad Friedel watched nervously as Fabian Schar's free-kick drifted just wide and Salah then found space in the box but shot over.
Basel dropped deep in an attempt to keep Spurs' attack at bay. It would take something special to breach their two rigid banks of four, and that was exactly what Jan Vertonghen produced in the 23rd minute.
The Belgian sliced open the Basel defence with a pass that left Dragovic flat on his backside and Dempsey rounded the goalkeeper before slotting in to an empty net.
Villas-Boas jumped for joy - but he was soon cursing his luck after Mousa Dembele's error allowed Basel to level.
Mohamed El-Nenny intercepted a sloppy pass from the midfielder and worked the ball out wide to Marco Streller, who cut open the Spurs defence to find Salah - who poked the ball past Friedel.
A series of flares went off in the home end and the away side went in to panic mode, giving the ball away easily.
Michael Dawson saved Tottenham's skin twice with goal-saving challenges on Salah and Streller.
Tottenham offered little at the other end and they trudged off the sodden pitch at half-time angry at having yielded the lead.
Spurs started the second half more lively, with Adebayor testing goalkeeper Yann Sommer, but Basel raced up the other end and won a corner thanks to Friedel's hesitancy in dealing with Streller.
And Tottenham were made to pay from the resulting flag-kick as Friedel palmed Schar's header straight to Dragovic, who smashed in from close range.
Dragovic came within inches of giving Basel a two-goal cushion just before the hour, before Villas-Boas ended Dembele's dismal night, replacing him with Tom Carroll.
With 17 minutes left Sommer saved well from Dawson's header, but Basel still looked as if they would hold on.
That changed in the 83rd minute, however, when substitute Huddlestone delivered a well-crafted chip that Dempsey drilled under Sommer.
Vertonghen made life tougher for his team when he tripped Streller as he ran through in the 90th minute and received a straight red card.
Dawson, lucky to escape a booking earlier in the match, saw yellow for a foul on Dragovic and tempers flared - with Streller and Walker going head to head just outside the box.
Basel dominated the first half of extra-time, with El-Nenny rattling the woodwork from 30 yards and Marcelo Diaz curling wide.
Dawson put his body on the line yet again as Basel piled forward, blocking Alexander Frei's shot with eight minutes of extra-time left.
Spurs held on for penalties - but Huddlestone missed Tottenham's first spot-kick to give Basel the advantage and Adebayor then skied Spurs' third while Schar, Streller and Fabian Frei all scored.
Diaz was left with the chance to clinch victory and he made no mistake, firing home to Friedel's left.