The pressure on Tim Sherwood and Tottenham cranked up a gear as their hopes of reaching the Europa League quarterfinals were made remote by Benfica's comprehensive 3-1 victory in North London.
Sherwood publicly criticised his players after Saturday's embarrassing 4-0 defeat to rivals Chelsea, which midfielder Sandro revealed led to a furious two-hour crisis meeting at Stamford Bridge.
However, there was to be no morale-boosting response in this last-16 tie against Benfica, who are now overwhelming favourites to progress ahead of next week's second leg.
Bolton loanee Rodrigo opened the scoring, slotting home after a tremendous Ruben Amorim ball just before the half-hour mark.
Emmanuel Adebayor uncharacteristically dragged wide in the second half when well placed, and the missed chance allowed the visitors to take control as woeful defending allowed Luisao to divert home, before Christian Eriksen reduced the deficit with a wonderful free-kick.
However, Spurs never looked likely saving their 11-match unbeaten European record at White Hart Lane as Luisao smashed home his second of the night, with Sherwood and counterpart Jorge Jesus refusing to shake hands at the final whistle.
Second-half substitute Mario Gomez struck a 79th-minute equaliser to put Fiorentina in the driving seat of their last-16 clash with Juventus following a 1-1 draw.
Gomez, who came off the bench in the 67th minute, cancelled out Arturo Vidal's third-minute opener in Thursday's first leg in Turin.
Juve had plenty of chances to double their lead and were unlucky not to go into the interval 2-0 up after Vidal's header struck the crossbar.
Jackson Martinez scored the only goal in the 57th minute as Porto claimed a 1-0 first-leg advantage over Napoli in their last-16 clash in Portugal.
The Colombian striker hit a left-footed diagonal shot past Napoli goalkeeper Pepe Reina to give his side the edge heading to Italy next week.
Carlos Eduardo had previously beaten Reina in the opening half but his goal had been disallowed for offside. The victory at the Dragao stadium maintained a perfect start for new coach Luis Castro, who replaced Paulo Fonseca last week after his promotion from the B team and claimed a 4-1 win against Arouca in his debut.
AZ Alkmaar put themselves in the driving seat in their tie against Anzhi Makhachkala, nicking a 1-0 lead in the opening leg in Holland.
A first-half penalty from U.S. international Aron Johansson settled the contest in AZ's favour and helped them erase memories of a 5-0 thrashing by the Russians when the two sides met in Alkmaar in last season's Europa League play-offs.
Valencia virtually assured themselves of a quarterfinal place after a remarkable 3-0 win at Ludogrets.
The Spaniards went 1-0 up through Antonio Barragan after five minutes but looked in trouble when Seydou Keita was sent off in the 25th and gave away a penalty in the process. Diego Alves kept out Roman Bezjak's spot-kick, though, and the visitors went on to add more goals through Federico Cartabia and Philippe Senderos.
Stunned Ludogrets then had a man of their own sent off, Juninho Quixada, to cap a miserable night.
Real Betis stunned city rivals Sevilla with a 2-0 win despite being outplayed for much of the first leg of their last-16 derby.
Sevilla had won their previous four games in all competitions and were six unbeaten, and they dominated Thursday night's game.
They somehow came away facing an imposing second-leg test next week, though, after Leo Baptistao's first-half header and Salva Sevilla's well-taken second gave Betis victory.
Lyon took a huge step towards the quarterfinals as they came from behind to claim a 4-1 win over Viktoria Plzen.
Tomas Horava took advantage of some poor defending from the Ligue 1 side in the opening minutes to claim an early lead before the score was levelled by Gueida Fofana 10 minutes later.
Alexandre Lacazette gave Lyon the lead early in the second half before Arnold Mvuemba claimed a valuable goal ahead of the trip to the Czech Republic for the second leg with Fofana's second adding gloss to the win.
Basel ended Salzburg's 14-game winning streak in all competitions as they played out a 0-0 draw in their first-leg tie at St Jakob Park.
Salzburg last tasted defeat against Rapid Vienna on November 24 and while they remain unbeaten in the competition, they were unable to take an advantage back to Austria for the second leg of the tie.