Kaboul launches the ball long towards Adebayor and Soldado in a desperate route-one approach to try and force an opening but Benfica repel their efforts with ease before Cardozo is penalised for a foul on Vertonghen.
90'
Gaitan's impudent chip nearly catches out Lloris on the break for Benfica but the Spurs shot-stopper is able to catch the ball and the visitors' advantage remains at two.
88'
Benfica make their third and final substitution as Lima is thrown on, with Jesus possibly looking for a fourth goal to really cap off an impressive night for the Portuguese league leaders. He replaces goalscorer Rodrigo for the final throes of this game.
87'
Lima enters the game and replaces Rodrigo.
86'
Sherwood and Jesus were involved in a heated war of words there and Jesus seemed to gesture towards the Spurs boss for the first goal too. He responded to Luisao's thumping finish by wagging three fingers in the general direction of Sherwood, who had clearly seen enough.
84'
Luisão has scored a goal for Benfica!
GOAL! Luisao surely wraps it up for the visitors with a powerful strike as Spurs once again concede from a set piece. His central defensive partner Garay heads towards goal but Lloris can only parry and the ball falls to the Brazilian who emphatically lashes the ball into the roof of the net off the underside of the crossbar. Sherwood's frustrations boil over on the touchline, with Benfica manager Jorge Jesus wildly celebrating his side's goal and possibly provoking the Spurs boss with his gesture.
82'
N. Bentaleb enters the game and replaces Sandro.
Two yellow cards in quick succession as Amorim enters the book for a late challenge on Naughton before Vertonghen comes flying in on Gaitan, who just appeared to have nipped the ball away before the Belgian slid in. Spurs do belatedly make their third change, with Bentaleb coming on in place of Sandro.
81'
J. Vertonghen gets yellow.
Rúben Amorim gets yellow.
80'
Spurs are believed to be readying Bentaleb to come on for the previously booked Sandro but are forced to delay the replacement as Jan Vertonghen heads to the touchline for treatment after trapping his studs in the turf.
78'
Kaboul is forced into a foul after the latest Spurs attack breaks down in Benfica territory and there are signs of tangible frustration amongst the hosts' ranks now.
Minute
Description
76'
D. Rose enters the game and replaces K. Walker.
Roberto Soldado comes on for a rather subdued Kane and Walker also comes off, with Danny Rose taking his place. On the pitch, Adebayor is in an offside position once again as he looked to trap the ball onto his chest.
75'
Soldado enters the game and replaces H. Kane.
74'
HOWLER! Lloris almost hands the lead back to Benfica with a poor piece of goalkeeping as he allows a speculative long ball to bounce over his head and on towards Rodrigo but the Frenchman partially redeemed himself by clawing the ball out for a corner with an outstretched left glove.
72'
Kaboul is single-handedly trying to lead the Spurs fightback and, having blocked an Amorim shot on the edge of their own area, sends Lennon away down the right, but the winger's cross is blocked off eventually.
70'
Eriksen sends a ball into the area from a free-kick and it is nodded back across goal by Kaboul, but Adebayor cannot get to the loose ball ahead of Oblak.
68'
Adebayor temporarily leaves the field to receive treatment and Benfica look to take advantage, but Spurs withhold their latest wave of pressure.
66'
E. Pérez enters the game and replaces M. Sulejmani.
Benfica make a double change, with Enzo Perez and Nicolas Gaitan entering the fray for Sulejmani and Cardozo respectively, with the latter nearly adding a third after a break-away move led by Rodrigo.
65'
N. Gaitán enters the game and replaces Ó. Cardozo.
64'
C. Eriksen has scored a goal for Tottenham Hotspur!
GOAL! What a strike by Eriksen, who reduces the arrears with a simply stunning free-kick. It was the Dane who helped earn the free-kick after some intelligent link-up play with Kane and his answer from the dead ball is to whip it over the wall and into the roof of Oblak's net.
62'
Sílvio gets yellow.
Spurs are readying substitutions, with Andros Townsend sent to warm up on the far touchline by Sherwood. Meanwhile, Markovic is flagged offside from a long Siqueira pass before Kane is upended on the edge of the box by a rash Silvio challenge following some neat work between the striker and Eriksen.
60'
Eriksen looks to lead the Spurs charge at the Benfica goal but his cross is excellently cleared by Ezequiel Garay, who did well to get in front of Kane, who was lurking at the near post.
58'
Luisão has scored a goal for Benfica! Assist by Rúben Amorim.
GOAL! Luisao doubles Benfica's advantage and that could bring the curtain down on Tottenham's European adventure after some woeful defending. The ball is squandered initially in midfield to Amorim and the midfielder advances before forcing Lloris to tip over. The same man goes across to the far side and whips in a corner straight onto the head of a criminally unmarked Luisao, who duly accepts the invitation to head home.
56'
Paulinho looks to send Eriksen hurtling through but his toe-ended pass hits Adebayor, who is stood in an offside position in front of the Dane and another Spurs attack breaks down.
54'
We have reached a slight lull in the game after the two sides traded chances early on in the half, with Benfica content to let Spurs play in their half before nicking the ball and hitting them on the counter.
52'
Oblak's long throw is intercepted by Naughton and he attempts to launch a Spurs riposte but Benfica are able to hold out easily once again. They have been breached just once, with the Adebayor opportunity, and are looking to keep it that way.
50'
And now it's Benfica's turn to go close after some more suspect Spurs defending. A simple long ball is flicked on by Cardozo into the path of Rodrigo, but the goalscorer strangely elects a first-time lob which fails to trouble Lloris when he had time to bring the ball down before shooting.
48'
MISS! Adebayor squanders a great chance to pull Spurs level as he drags his shot horribly wide after some great work from Eriksen in slipping the ball through the heart of the Benfica backline. He really ought to have scored and may not get a better opportunity.
46'
The two teams are back on the field and Spurs get the ball rolling once more for this second half.
43'
His stats suggest otherwise, having conceded once in his last 11 appearances, but Oblak looks decidedly suspect in the Benfica goal. His kicking is cause for hope in the Spurs team at present, with two successive efforts going more up than out.
41'
Spurs are failing to click in attack here and Benfica almost break again but the ball is played in between Rodrigo and Markovic, who are both unable to profit.
39'
Adebayor is penalised once again for grappling with Luisao, with Spurs' frustrations epitomised by the consant speculative high balls being sent in the hitman's general direction.
37'
Spurs are guilty of over-playing at times, with Naughton fortunate to get the ball out of his feet and clear with Benfica hunting in packs to win the ball back off their wounded opponents.
35'
Sandro is penalised for another foul and must begin to be slightly more reserved with his tackling, especially having been handed a yellow card early on here.
33'
Lennon looks to get his side back on the front foot immediately and wins a corner off his marker Siqueira but the delivery is poor and Markovic is easily able to clear.
31'
It could be a bitter blow for Spurs, with Benfica surely now content to hit their hosts on the counter with the advantage of an away goal. Spurs simply cannot afford to concede another.
30'
Rodrigo has scored a goal for Benfica! Assist by Rúben Amorim.
GOAL! Benfica take the lead through Rodrigo and they have deserved that for their efforts in the last few minutes, having ramped up the pressure on the Spurs goal. Ruben Amorim steps onto the ball in midfield and releases a pass inside Naughton to the Spaniard, who kept his cool to tuck a sumptuous finish underneath Lloris.
27'
The Spurs defence suffers two brief lapses in concentration but Lazar Markovic fails to capitalise after a direct run into the area, with his cut-back lacking sufficient purchase. Adebayor sloppily hands the ball back to Benfica but Kaboul steps in to deal with Cardozo as the Paraguayan looked to turn.
25'
Kaboul's header sails downfield and almost catches out Oblak as Eriksen chases the ball down with the keeper, but the Slovenian is alert enough to back-track and claim the ball before the Dane can tap into the unguarded net.
23'
Eriksen is the latest to be in an offside position as another Spurs attack breaks down from a long pass over the top of the Benfica defence.
21'
Siqueira is also called back for being in an offside position before Spurs force another succession of corners, which Cardozo is forced to hack away under pressure from the lively Kane.
19'
Luisao is forced to concede two corners in succession as Spurs threaten to up the ante but eventually the ball is cleared. Kane nods a speculative pass onto Paulinho seconds later, but he is flagged for offside before he can release his shot, which goes wide anyway.
17'
Spurs slowly starting to grow into the game but their progress is halted when Adebayor finds himself in an offside position from Walker's crossfield pass.
15'
Eriksen looks to feed Lennon into the area but Luisao blocks the pass off, before the former finds Sandro on the edge of the area. The Brazilian's piledriver, however, flies high over the crossbar. First real opening for the hosts and it was a good move, even if it lacked the finish to match.
13'
Both sides are looking to gain control of this contest but are losing possession slightly cheaply in midfield areas and neither side has got a real rhythm going as yet.
11'
Walker delivers a free-kick from the right flank in towards the head of Kaboul but he is adjudged to have fouled goalkeeper Jan Oblak. The decision looked slightly harsh on the Spurs man.
9'
Sandro gets yellow.
Spurs win a free-kick of their own but when it is cleared, Sulejmani pounces onto the loose ball and drives at the Spurs defence. His progress is cut short, however, by an unceremonious Sandro challenge which sees the Brazilian enter the book.
7'
Kane wins a long ball and flicks on in the direction of Adebayor but the Togolese is not quite on the same wavelength as his strike partner. Moments later, Walker's trip on Guilherme Siqueira results in a free-kick, which is lofted towards Luisao, but his downward header is gathered by Hugo Lloris.
5'
Eriksen is adjudged to be offside after Naughton's searching pass down the line looks to free the Dane, who has started the match brightly.
3'
Silvio looks to escape down the right flank but cannot quite keep the ball in play. Benfica have controlled the game in the opening exchanges here at White Hart Lane.
1'
We are underway as Benfica get the ball rolling.
Good evening and welcome to this LIVE commentary of Tottenham Hotspur's Europa League clash with Benfica, as we enter the round of 16 in the competition. My name is Tom Marshall-Bailey and I will be bringing you all the latest developments this evening from White Hart Lane.
Tottenham make three changes to the side which lost 4-0 at Chelsea on Saturday, with interim manager Tim Sherwood opting to field young Harry Kane up front alongside Emmanuel Adebayor, while Paulinho and Christian Eriksen are also recalled.
Here are the teams in full starting with the hosts. Spurs: Lloris; Walker, Kaboul, Vertonghen, Naughton; Lennon, Sandro, Paulinho, Eriksen; Adebayor, Kane. Substitutes: Friedel, Fryers, Rose, Bentaleb, Chadli, Townsend, Soldado.
Benfica make four changes from the team that beat Estoril 2-0 at the weekend, with Miralem Sulejmani, Ruben Amorim, Silvio and the dangerous Oscar Cardozo all starting for the Portuguese side.
It's only Harry Kane's second start this season and a meeting with the Portuguese side represents a real baptism of fire for the 20-year-old this evening. Younes Kaboul, yesterday boosted by having his red card in the defeat to Chelsea rescinded, captains the side tonight.
Sherwood, of course, will be hoping to bounce straight back to winning ways after the mauling at Stamford Bridge as their top-four pursuit took a hit and with a North London derby sandwiching the two legs of this Europa League tie, a win tonight is imperative.
The fact he is also able to call on Eriksen is an added boost to the caretaker coach, with the Dane inspiring Spurs to their comeback win over FC Dnipro Dnipropetrovsk in the last round by scoring a free-kick and teeing up Emmanuel Adebayor for his first of two goals.
Spurs sorely lacked a creative spark against Chelsea, with Kyle Walker and Gylfi Sigurdsson deployed on the flanks and Aaron Lennon just in behind Adebayor so Eriksen's return will be warmly greeted by manager, players and fans alike.
Benfica's fortunes are slightly contrasting given that they stretched their lead over second-placed Sporting Lisbon to seven points at the weekend with a 2-0 win over Estoril. Spurs will have to be alert to deal with one half of a 24-goal strikeforce in Rodrigo this evening, with the hitman scoring again at the weekend.
His partner in crime Lima is left on the bench this evening but Benfica followers should not be alarmed at that news given that Oscar Cardozo, a scorer in last year's final, is in to replace him.
Spurs are hosting the Portuguese giants for the first time since they met in the European Cup semi-final in 1962. Benfica won that tie and went on to beat Real Madrid 5-2 in an astonishing final.
STAT: Spurs have an impressive recent record against Portuguese opposition in European competitions having won seven out of their last 10 encounters, losing twice and drawing once in the process.
Equally, though, Benfica come into this game having won 21 of their last 23 fixtures in all competitions. It's sure to be a highly-competitive game between two good teams and we are moments away from kick off.
HALF-TIME: Tottenham 0-1 Benfica. Spurs deservedly find themselves here, with Rodrigo cashing in on some woeful defending from Naughton to slot home confidently and hand his side the lead. The visitors had been threatening in the stages building up to the opener and now have something to hold on to and exploit Spurs' defensive deficiencies on the counter. The hosts have offered precisely nothing up top, with Sherwood's gamble on unleashing Kane failing to pay off in the opening period.
FULL-TIME: Tottenham 1-3 Benfica: Off the back of a 4-0 humbling at London rivals Chelsea, this was not the tonic for Spurs interim manager Sherwood, whose side were comprehensively outplayed by a rampant Benfica side. Rodrigo's superb first-half finish put them on their way before Luisao doubled the lead with a free header. Eriksen's magnificent free-kick gave Spurs hope, but it was quickly distinguished by a thumping finish from Luisao to give the hosts an uphill battle in Portugal in a week's time.
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