Tottenham experienced defeat for the first time in this season's Uefa Cup as they lost 2-1 to Sevilla in the first leg of their quarter-final clash.
In the terraces there was trouble between Tottenham supporters and police in scenes that were reminiscent of the Stadio Olimpico on Wednesday, while on the pitch Martin Jol's side battled hard but ultimately went down to a narrow loss.
Robbie Keane gave Spurs a dream start but the game turned on 19 minutes when Sevilla were awarded a controversial penalty, which was dispatched by Fredi Kanoute.
Alexander Kerzhakov then scored the winner before half-time, before an uninspiring second half left the tie delicately poised ahead of next week's return leg at White Hart Lane.
Clean sheets have been hard to come by against Tottenham over the last two months and it took just 68 seconds for Keane to kill off any hope Sevilla had of not conceding an away goal.
Spurs had already seen a penalty appeal for handball waved away when Dimitar Berbatov slid in Keane and the Irishman slotted home at the second attempt after seeing his first effort parried by Andres Palop.
Daniel Alves, identified as one of Sevilla's main threats, had to be carted from the field a minute later after sustaining an injury as the home side's nightmare start continued.
Alves returned after one or two anxious moments and Sevilla finally started to settle, with Tottenham content to let them enjoy the bulk of possession.
Sevilla drew level when Paul Robinson was adjudged to have brought down Adriano Correia, although replays showed the goalkeeper had taken the ball cleanly.
Robinson was enraged and his protests earned him a yellow card, but former Tottenham striker Kanoute had no trouble keeping cool and tucked his spot-kick assuredly into the bottom right corner.
Keane almost silenced the crowd's celebrations within seconds off the kick-off, as he cut in from the left wing and forced a fine save out of Palop.
The game started to fluctuate thrillingly from end to end and Robinson had to be at his most athletic to tip away Jesus Navas' long-range strike, before making a more routine save off Kanoute.
Sevilla managed to take the lead before half-time as Michael Dawson failed to clear Navas' cross and Kerzhakov nodded home Julien Escude's headed pass after 36 minutes.
The second half did not start as superbly for Tottenham as the first had, but they pushed Sevilla onto the back foot and Keane nearly supplied a deserved equaliser as he dragged a shot wide from the left-hand side of the box.
Jermaine Jenas also hit a free-kick wide, while Aaron Lennon started to have more of an influence on the game with some lightning sprints down the right wing.
Sevilla remained dangerous on the counter-attack and Kanoute twice came close to grabbing his second of the evening, first slamming wide from distance and then heading off target from Navas' cross.
Both Lee Young-pyo and Paul Stalteri appeared to be suffering from knocks but Jol decided against bringing on rookie defender Philip Ifil, instead bringing on Steed Malbranque and Hossam Ghaly for Lennon and Teemu Tainio.
Malbranque had one good opportunity five minutes from time but failed to connect properly from eight yards out, to leave Tottenham needing victory in the second leg.
All four quarterfinal matches occurred Thursday in the UEFA Cup, with all three Spanish sides remaining in the competition winning their games.  Only one match ended in a draw, that being the game between AZ Alkmaar and Werder Bremen.