Tottenham Hotspur face an uphill task to make the quarter-finals of the Europa League after falling to a 3-1 defeat in the first leg of their last-16 tie with Benfica.
Spurs dominated the opening 30 minutes, but they conceded the opening goal when Rodrigo advanced behind the Tottenham defence to slide the ball past Hugo Lloris.
Luisao doubled Benfica's advantage after the break, and although Christian Eriksen halved the deficit with a stunning free kick from 20 yards, Luisao netted his second of the game six minutes from time to help his team to a valuable triumph.
Read below to see how the action unfolded at White Hart Lane.
Hello, and welcome to Sports Mole's coverage of the match between Tottenham Hotspur and Benfica in the last 16 of the Europa League.
For much of their last-32 clash with Dnipro, Spurs looked second best and appeared to be heading out of the competition when they were left requiring three goals in the final 40 minutes. However, the North London outfit found the goals that they required during a remarkable second-half turnaround to earn a highly-anticipated tie with Benfica.
The team news is in from White Hart Lane. Full details to follow.
TOTTENHAM HOTSPUR XI: Lloris; Walker, Kaboul, Vertonghen, Naughton; Lennon, Paulinho, Sandro, Eriksen; Adebayor, Kane
BENFICA XI: Oblak; Luisao, Garay, Pereira, Guilherme Siqueira; Fejsa, Perez, Cardozo, Lima; Rodrigo, Markovic
TOTTENHAM HOTSPUR SUBSTITUTES: Rose, Soldado, Townsend, Chadli, Friedel, Fryers, Bentaleb
BENFICA SUBSTITUTES: Artur Moraes, Djuricic, Lima, Gaitan, Jardel, Almeida, Perez
The selection in the Spurs starting lineup that catches your eye is the inclusion of Harry Kane over Roberto Soldado. The 20-year-old Englishman has only netted once in 11 appearances this season, but he has been given the nod over the experienced Spaniard. Spurs are without captain Michael Dawson, with Younes Kaboul deputising in the centre of defence.
Tonight's encounter will be the first time that these two teams have met at White Hart Lane for over 50 years. Their last fixture came in 1962 when they faced each other in the European Cup, with Benfica prevailing on that occasion. Will history repeat itself this evening?
I should point out that this evening's match is the first of a two-legged tie, the second of which takes place in Portugal in a weeks time. Benfica will be expected to earn a result on their home patch so it's important that Spurs gain at least a draw tonight.
PREDICTION! This match has got a low-scoring draw written all over it, but both sides have the quality in their ranks to put on a show tonight. I think both sides will net, but that could be their only successful effort on goal. 1-1.
The two teams have walked out onto the pitch at White Hart Lane. We will be underway shortly!
Benfica get us started. They will be after a quick start to impose themselves on this tie.
It's all extremely tight in the middle of the park, but Spurs win the first exchange with at least half-a-dozen men surrounding the ball. However, a direct ball to Emmanuel Adebayor is lost, and Benfica win back possession.
There has been no efforts on goal so far, but it's made for an interesting opening. Spurs have placed particular emphasis on attacking down the left-hand side, while Benfica seem comfortable with leaving men forward for the breakaway.
Benfica win a free kick in a threatening position on the left-hand side, but despite winning the ball in the penalty area, his header bounced into the hands of Hugo Lloris.
BOOKING! Sandro goes into the book for a cynical block on Miralem Sulejmani. The blame has to go to Christian Eriksen though, after his weak set piece was easily intercepted by the Benfica backline.
As you would expect, Benfica look a class above anything that Spurs have faced so far in this competition. The Portuguese giants bowed out of the Champions League with 10 points in a group that involved Paris Saint-Germain, so it goes without saying that they are one of the favourites to repeat last year's appearance in the final.
Spurs are enjoying a sustained spell of possession, but their final ball is lacking in accuracy. A move from the right-hand side ends up with Sandro on the edge of the penalty area, but his first-time effort flies into the top tier of the stand.
An excellent searching ball from Kyle Naughton is headed back across goal for Emmanuel Adebayor, but a Benfica defender gets back to divert the ball behind for a corner. However, two successive deliveries fail to beat the first man and Benfica have a free kick.
Spurs have won four or five corners during the last few minutes but the Benfica defence is packed and it looks a difficult task to win an aerial ball. All Spurs at the moment though.
Benfica can't get a hold of the ball at the moment. Spurs are dictating all of the play, but they haven't threatened Jan Oblak's goal as much as they should have done.
Spurs surge forward through Kyle Walker but he just overhits the ball on his attempt to take it past the defender and Benfica are able to clear. Moments earlier, Benfica had threatened a counter attack through Lazar Markovic, but he miscued his attempted pull back to the edge of the box.
GOAL! Tottenham Hotspur 0-1 Benfica (Rodrigo)
Out of nowhere, Benfica have the lead at White Hart Lane. A sublime ball from midfield cut open the Tottenham defence, and Rodrigo advanced behind Kyle Naughton to dribble into the penalty area before coolly slotting the ball past Hugo Lloris.
Well that wasn't in the Spurs script. They have been the better side, but they have nothing to show for all their possession. They need to get to half time without conceding another or else it's a long way back from conceding two away goals.
Sandro is running a very tight line. He has already been booked, but it isn't stopping him rushing into challenges, needless ones at that. It might be worth bringing him off at the break.
That Benfica goal has sucked the life out of the Tottenham support. They have been very quiet since Rodrigo's opener, while the visiting fans make plenty of noise behind the goal.
Spurs insist on playing a long ball to Emmanuel Adebayor, but they are having no joy whatsoever with the tactic. Harry Kane is dropping too deep to benefit from any loose ball that might come from a stray header too. Spurs need half time.
HALF TIME: Tottenham Hotspur 0-1 Benfica
There will be no added-on time at White Hart Lane, and Spurs go into the break a goal behind to Benfica. It's been a game of little action, but Spurs can have no complaints to being a goal adrift. They have looked abject in attack.
The fact that there were just three shots on goal during that first half tells you everything that you need to know about that opening 45 minutes, with the only effort on target being the goal. Spurs have dominated possession, but they have done nothing with it.
Will Tim Sherwood make changes for the second half? On their current showing, Spurs will find it difficult to break down a resolute Benfica defence who will only have grown in confidence after Spurs' failure to test them in the first half. Roberto Soldado is an option, but would be offer any more threat to that of the current attack?
The two teams have returned. It will be Spurs to get the match back underway. No changes from either side.
CHANCE! Huge chance for Spurs. Christian Eriksen does superbly in the centre of the pitch before dinking the ball through to Emmanuel Adebayor. The striker has plenty of time to try to find the bottom corner, but he drags his effort harmlessly wide. A big let-off for Benfica.
Miralem Sulejmani has been on the biggest threats for Benfica, and the Serbian does well to advance towards the penalty area, but after play a one-two with a teammate, the ball bounces out for a throw-in.
SHOT! Aaron Lennon controls a floated ball on his chest, but after drifting inside onto his left foot, his shot is weak and straight at Jan Oblak from 20 yards.
Spurs are much improved in this second half, but it hasn't put off Benfica. They are continuing to throw men forward on the break.
GOAL! Tottenham Hotspur 0-2 Benfica (Luisao)
Game over? Spurs have a mountain to climb in this tie. A mistake from Harry Kane allowed Benfica to get a shot on goal and earn a corner. From the resulting set piece, Luisao rose above everyone to glance the ball past Hugo Lloris with very little attention from the home side's defence.
It's imperative that Spurs don't concede again. Benfica are in complete control of this tie, and a third goal will all but seal their place in the last eight. Changes for Spurs are imminent.
BOOKING! Harry Kane drives towards the penalty area and wins a free kick 20 yards from goal after being felled by Silvio, who was promptly cautioned by the referee.
GOAL! Tottenham Hotspur 1-2 Benfica (Eriksen)
What a strike! There was little alternative to Christian Eriksen taking the free kick, but why would anyone else be in contention when he can strike the ball like that! The Dane powers a right-footed shot over the wall into the top corner, leaving Jan Oblak with no chance!
Spurs needed that! Since the goal, Benfica have attempted to exploit any gaps in the Spurs defence, with the danger being that the home side are getting over confident with throwing men forward. They still need to ensure that no goals are conceded at the other end.
Those changes that I mentioned earlier seem to have been scrapped for now, but Emmanuel Adebayor and Aaron Lennon are apparently carrying knocks. It wouldn't be a bad idea withdrawing Sandro because he continues to run the risk of earning a second yellow card.
CHANCE! Hugo Lloris is a lucky, lucky boy! The Frenchman came out of goal to head clear a long ball over the defence, but he misjudged the bounce and saw the ball go behind him. Fortunately for the stopper, he was able to dive in to prevent Rodrigo nicking his second goal of the night.
SUBSTITUTION! Roberto Soldado has been introduced for the final 15 minutes of the match, with Harry Kane making way for the Spaniard.
SUBSTITUTION! Kyle Walker is also being withdrawn by Tim Sherwood, with Danny Rose being thrown on in his place. Walker appeared to be limping when he left the pitch.
The chances have dried up for Spurs over the past 10 minutes. Can they manage one final push in the final 10 minutes?
BOOKINGS! Ruben Amorim goes into the book for a poor challenge on Kyle Naughton. Less than a minute later, Jan Vertonghen is cautioned, meaning that the Belgian will be suspended for the second leg next week.
GOAL! Tottenham Hotspur 1-3 Benfica (Luisao)
That could be the decisive goal in this tie. Hugo Lloris pulled off a terrific save from the initial header, but the ball rebounded to Luisao, who powered home an unstoppable effort from six yards out to leave Spurs' Europa League hopes in tatters.
It's all kicking off on the bench, too. Jorge Jesus appeared to hold three fingers up to the Spurs bench after they had netted their third goal, and Tim Sherwood has reacted angrily to the gesture. The two managers needed to be separated by the fourth official.
There will be three minutes of added-on time.
Benfica are doing a good job of retaining possession. This game is as good as over.
FULL TIME: Tottenham Hotspur 1-3 Benfica
The full-time whistle has gone at White Hart Lane, and Spurs have fallen to a disappointing 3-1 defeat at the hands of Benfica. The home side made inroads during an improved second-half display, but the Portuguese outfit had far too much class for Tim Sherwood's team.
The second leg takes place in Portugal in seven days' time, but Spurs face an immensely tough ask to progress to the last eight. They will need to score a minimum of three times to have a chance of advancing through to the quarter-finals.
That will be all from Sports Mole this evening. Thank you for joining us this evening, and we hope to see you again for all of the action around Europe at the weekend. Goodbye for now.
