Tottenham crashed out of the Europa League quarter-finals on penalties following a 2-2 second-leg draw against Swiss outfit Basel.
The match had finished level in normal time, with Clint Dempsey's early strike putting Spurs in control of the tie, but they were quickly pegged back thanks to Mohamed Salah's near-post finish.
Basel capitalised on slack defending just after the interval to take control as Aleksandar Dragovic rifled home from close-range after Brad Friedel had parried a Fabian Schar header.
Plucky Tottenham were not to be denied, as Dempsey netted his second following a searching pass from substitute Tom Huddlestone, before Jan Vertonghen's red card prior to the final whistle left the visitors with an uphill task for extra-time.
Spurs held on with last-gasp defending against Murat Yakin's outfit, but ultimately to no avail as Basel won the shootout 4-1 after Huddlestone and Emmanuel Adebayor missed from 12 yards.
In a dull opening, Fabian Schar was the first to chance his luck, firing in a low free-kick which flew just wide of Friedel's near post.
Schar and his defensive partner Dragovic had been largely composed in the opening exchanges, with both rearguards on top, but the latter was badly at fault as Tottenham seized a crucial advantage in the tie at the midway point of the first half.
Vertonghen's speculative pass through the middle appeared harmless but Dragovic failed to deal with it and in nicked Dempsey, who rounded the goalkeeper before coolly rolling the ball into the unguarded net.
Their lead, however, did not last long.
Mousa Dembele was caught napping in midfield by Marco Streller, who laid the ball off to the onrushing Salah and, despite a heavy touch, he toe-poked the ball beyond the reach of Friedel at his near post.
The Egyptian almost stole in for a second moments later but could not quite prod past the alert Friedel before fellow goalscorer Dempsey rose well at a corner only to head straight at Yann Sommer.
Sommer had to go one better before the break as he sprung to his right to push away Dembele's curling strike before getting down low to hold on to an Adebayor effort from the subsequent attack in the last meaningful action of the half.
The Togolese striker registered the first notable attempt after the interval as he nodded down a corner which Sommer was able to gather.
From a set-piece of their own, Basel moved ahead for the first time on the night and strengthened their grip on the tie.
A flick-on by Schar at the near-post was inexplicably pushed out by Friedel to the unmarked Dragovic, who atoned for his earlier error by slamming into the roof of the net from a couple of yards out.
The Swiss defender almost doubled his tally as he connected perfectly with Fabian Frei's inswinging free-kick, but his header floated just wide of the upright.
Given the defiant nature of the Swiss side's defence, Spurs found an equaliser against the run of play.
Substitute Huddlestone sent a raking pass to Dempsey, who managed to send a volley goalwards. The ball somehow crept underneath Sommer, who appeared to dive too early, to breathe new life into the tie.
Vertonghen struggled with the constant movement of a willing Streller and as the tie approached extra-time, Spurs' task was made all the more difficult after the Belgian tripped the striker as he rushed through on goal.
As the last man, referee Olegario Benquerenca had no choice but to dismiss the centre-back.
Basel pushed for a winner in extra-time against a tiring Spurs outfit, but it was not to be as the tie moved onto a dramatic shootout.
Huddlestone's effort was saved by Sommer, before Adebayor blazed horribly over. It left Marcelo Diaz with the task of putting his side into the semi-finals, and the Chilean made no mistake from the spot.