Last Updated: 20/03/14 8:09pm
So close for Spurs, but their late rally was too late in the end. That's all for tonight's commentary. Thanks for joining me. Report and reaction to follow.
Another Spurs chance! Chadli floats a cross in from the right and Kane, leaning back, gets his header on target but only into the arms of Oblak.
Sigurdsson heads down a left-wing cross and the ball is heading inside the far post, but Oblak gets across to make the save. So close!
A Spurs penalty appeal turned down! Harry Kane appears to be bundled over in the box by Sulejmani, but the Slovenian referee Damir Skomina looks to his assistant behind the goal and then waves play on.
Salvio meets a cross from the left and half-volleys the ball towards goal but it's straight at Friedel.
Lennon gets free down the right and reaches the ball ahead of Oblak. He squares for Sigurdsson but Luisao is there to clear.
Chadli does it again! The Belgian swivels and strikes home a shot from close range after a knockdown to give Spurs the lead on the night. If Tottenham can score again, they can take the tie to extra-time.
Chadli drives forward down the left channel after Harry Kane's pass and strikes a fierce shot from 25 yards which flies in to the right of Oblak. Great hit by the Belgian. Spurs need two more goals here.
Chadli has a shot on goal from the left side of the penalty area but Oblak easily claims his effort.
First change imminent. Looks like Enzo Perez will be entering the fray shortly. No sign of a Spurs goal - remember they need three to have any hope of going through.
Townsend cuts in off the left flank and fires a low shot that deflects just past the post. Better from Spurs.
Chadli crosses in from the left for the stretching Sigurdsson, but the Icelander can't connect and Oblak is able to get down and make a comfortable save.
AZ Alkmaar have already made it through to the quarter-finals tonight. They drew 0-0 at Anzhi Makhachkala tonight, having won the first leg 1-0.
Salvio and Maxi Pereira link up brilliantly in the box but Spurs manage to put the ball out for a corner.
Sandro makes another important interception in the area as Benfica attempt to mount an attack down the left.
Chris Green has emailed in to say: "Spurs have - to some extent - performed to an impressive standard so far, but the defending leading up to the goal was truly abysmal."
Half-time: Benfica 1 (Garay 34) Tottenham 0. Benfica lead 4-1 on aggregate. The hosts in control - they've had 61% possession in the first half - but Spurs have had more shots on goal.
Paul Marx in NYC joins us again: "Only bad pick was Townsend - he is not trying and making many mistakes. Needs to challenge for everything. Lennon off the pace a little, but I see him taking over in the second half. Football is great."
Spurs still have to score at least three goals here to have any hope of progressing to the quarter-finals. They've had chances, mainly those that have fallen to Soldado.
Siqueira is freed down the left but he can't quite reach the ball before it crosses the byline, and Friedel is able to take a goal kick.
Garay rises above Sandro to power home a header and extend Benfica's lead. The cross from Salvio came in the right, with Townsend seemingly beaten all too easily. 1-0.
Sandro has to be alert once more to intercept another low cross from the right from Maxi Pereira, ahead of Oscar Cardozo.
Another opening for Soldado but he can't get a clean shot away from the knockdown. Then Chadli heads the resulting corner wide of Oblak's right-hand post.
Fryers heads a Sulejmani cross from the left away. Townsend sprints downfield onto Chadli's pass, but Luisao clears.
Rose's battle with Salvio continues, with the Argentinian penalised for pushing the left-back to the ground.
Ruben Amorim receives treatment to his ankle after a midfield collision. He's OK to continue though.
The ball breaks loose from a corner for Soldado, who is played onside by Siqueira. The Spain striker, however, hits his shot into the ground and the chance is gone.
Sigurdsson does well to prevent a corner, but the set piece is then awarded when the ball appears to hit Townsend. The corner is initially cleared but the ball is crossed back in and Garay nods it across for Luisao to get a header in on goal, but the ball goes over.
Danny Rose makes a good recovery just outside the Spurs penalty area to stop the run of Eduardo Salvio.
Some Price Boosts for tonight's game. Skipper Aaron Lennon is 25/1 to score first, while a 2-0 Spurs win is priced up at 33/1 with Sky Bet. A 3-0 Benfica victory is 14/1. As for Jamie Redknapp's tips, he fancies Oscar Cardozo as the first goalscorer - that's a 4/1 shot.
Rohin Malhotra is not impressed by the Spurs selection tonight: "What an utterly disappointing line-up from Tim Sherwood. The fans want a result, the team needs a result, the travelling fans go in hope of a result. And yet Sherwood puts out a side/bench weaker than I can recall from any Spurs team for a few years. Gutted."
Paul Marx joins us from New York City to say: "Think Sherwood thought this one over very carefully. Chadli gives the height and aerial ability while at the same time being given the opportunity to make good on his Arsenal performance. Eriksen plays well with Kane and we will probably see them in the second half. Good luck to any of the new boys that get their chance tonight!"
The last team to stop Benfica from scoring in a competitive fixture was Olympiakos on November 5. They have scored in each of their last 25 matches in all competitions, in which they are unbeaten.
Spurs are trying to avoid a fourth defeat in a row tonight - the last time they suffered that kind of poor run was in April 2004.
Chris Green from Huddersfield thinks Spurs can achieve their aim tonight: "Tottenham to win 3-0, with Sigurdsson and Soldado (2) scoring the goals."
Zeeshan Cats has emailed in to say: "Very poor line-up from Sherwood. I don't see where the goals are going to come from. I also can't see how Tottenham are going to get three goals. As a Spurs supporter, I say we win 4-3 on agg. As we say to dare is to do. COYS!"
Spurs are 5/1 with Sky Bet to win at the Estadio da Luz on the night, and 12/1 to qualify through to the quarter-finals. Benfica 4/7 to win the second leg, and the draw is 16/5.
Sherwood's decision to make Aaron Lennon the captain tonight is generating a lot of interest. The 26-year-old is making his 340th appearance for Spurs in all competitions tonight.
Benfica won 4-2 at Nacional in the Portuguese Primeira Liga on Monday night to maintain their seven-point lead over Sporting Lisbon at the top of the table. Jorge Jesus' team shows four changes to the one that began the 3-1 first-leg win at Tottenham last Thursday. Argentina winger Eduardo Salvio is fit and starts, while Maxi Pereira, Filip Djuricic and Andre Gomes are also included. Silvio is suspended; Rodrigo and Lazar Markovic drop to the bench; and Ljubomir Fejsa is not involved tonight.
Jordan Archer is Tottenham's reserve goalkeeper tonight, while Harry Kane is another familiar name on the bench along with Eriksen. Less familiar are defenders Dominic Ball (centre-back), Milos Veljkovic (centre-back / holding midfielder) and Connor Ogilvie (centre-back / left-back), and versatile midfielder Harry Winks.
Tim Sherwood makes five changes to the Spurs team that lost 1-0 at home to Arsenal in the Premier League on Sunday. Brad Friedel replaces Hugo Lloris in goal. Zeki Fryers comes in at centre-back, with Jan Vertonghen suspended and Younes Kaboul injured. Sandro fills in in central defence, so Gylfi Sigurdsson comes into the midfield along with Aaron Lennon, who captains the team. Christian Eriksen drops to the bench. Emmanuel Adebayor is also injured, so Roberto Soldado leads the line.
And the Benfica bench: Paulo Lopes (GK); Jardel; Andre Almeida, Enzo Perez, Lazar Markovic; Rodrigo, Lima.
Here's the Benfica team for tonight: Jan Oblak; Maxi Pereira, Luisao (c), Ezequiel Garay, Guilherme Siqueira; Eduardo Salvio, Andre Gomes, Ruben Amorim; Filip Djuricic, Oscar Cardozo, Miralem Sulejmani.
Tottenham's starting line-up: Friedel; Naughton, Fryers, Sandro, Rose; Lennon (c), Bentaleb, Chadli, Sigurdsson, Townsend; Soldado.