Tottenham paid the price for conceding twice in the first seven minutes to crash out at the Uefa Cup quarter-final stage 4-3 on aggregate to Sevilla.
Sevilla are one of three Spanish teams in the semi-finals
Spurs had too much to do after Steed Malbranque's rash own goal and former player Fredi Kanoute's superb finish.
Substitute Jermain Defoe gave Spurs hope by scoring with his first touch and Aaron Lennon converted from close range as Spurs levelled on the night.
Spurs missed further chances while Teemu Tainio was sent off late on.
Sevilla will now play fellow Spanish side Osasuna for a place in the final as they continue the defence of their title, while Spurs are left to wonder what might have been.
The signs were ominous for the home team when Michael Dawson's slip in the opening seconds allowed Alexander Kerzhakov a run on goal, but the Russian's strike from a tight angle was easily saved by Paul Robinson.
Spurs failed to read the signs, though, and fell behind to a goal that had a whiff of panic about it.
Christian Poulsen's free header from Jose Luis Marti's corner appeared to be drifting wide but Malbranque rashly slashed at the ball and sliced it into his own net.
Kanoute should have doubled Sevilla's lead on the night seconds later, only to head Kerzhakov's cross wide from six yards.
But the striker who spent two years at White Hart Lane did stretch Sevilla's lead with a sweetly-constructed goal on seven minutes.
Kanoute lost his marker far too easily from a throw-in, cut inside to exchange passes with Kerzhakov and a nifty change of feet saw him pass the ball into the net.
Needing to score four to win the tie, Spurs had their first sight of goal when Dimitar Berbatov's pass released Robbie Keane but the Irishman's run took him wide and he crossed meekly into the keeper's arms.
Sevilla, though, were passing Spurs off the pitch, with Poulsen and Daniel Alves working in the space behind Kanoute - and with better finishing the Spanish team would have scored again before the break.
Chimbonda's slip allowed Alves to set up Kanoute, who had time to steady himself before firing wide from 18 yards, while the best move of the match saw Poulsen, Alves and Kanoute ping first-time passes about to set-up Adriano Correia, who wasted his shooting chance.
Adriano's fearsome pace took him past Tainio to pull the ball back for Kerzhakov, who fired straight at a relieved Robinson from 12 yards.
Steed Malbranque slashed the ball into his own net
Spurs needed the lift of a goal before half time but Berbatov's snap-shot struck the foot of the post with Cobeno beaten.
Tottenham increased the pressure after the break and pinned Sevilla in their own half.
Aaron Lennon emerged from an hour of anonymity to spark Spurs' best passing move, which ended with Zakora shooting meekly at Cobeno, who then safely gathered a Keane shot as the pressure mounted.
From looking down and out, Spurs invigorated the tie with two goals in as many minutes.
Defoe proved an inspirational substitution when he pulled a goal back, diverting Keane's shot into the goal seconds after his introduction.
For the first time, the holders looked rattled and Spurs shook them again when the ball bounced up kindly for Lennon to finish from close-range.
Sevilla served a reminder they still carried a threat and Robinson was twice called into action to save from Antonio Puerta as he thrust forward.
Still Spurs pressed but Dawson wasted a chance when he blazed over when the ball dropped to him eight yards out and the normally efficient Berbatov tamely shot straight at Cobeno from 10 yards.
Spurs' hopes ended when Tainio was sent off in injury time for a poor challenge on Antonio Puerta.
Tottenham: Robinson, Tainio, Dawson, King, Chimbonda, Lennon, Zokora (Defoe 65), Jenas, Malbranque, Keane, Berbatov.
Subs Not Used: Cerny, Murphy, Ghaly, Taarabt, Barnard, Ifil.
Sent Off: Tainio (90).
Booked: Dawson, Malbranque, Defoe.
Goals: Defoe 65, Lennon 67.
Sevilla: Cobeno, Hinkel, Javi Navarro, Escude, Puerta, Daniel (Renato 55), Poulsen, Marti, Adriano Correia (Aitor Ocio 69), Kerzhakov (Maresca 82), Kanoute.
Subs Not Used: Javi Varas, David, Luis Fabiano, Jesus Navas.
Goals: Malbranque 3 og, Kanoute 8.
Ref: Konrad Plautz (Austria).