The hosts took the lead in the first half when Ezequiel Garay rose highest inside the box to plant a header past Brad Friedel, giving his side a 4-1 lead on aggregate.
It appeared to be staying that way until a two-goal salvo from Nacer Chadli, who struck twice in as many minutes to send Spurs just one goal away from forcing extra time.
The visitors squandered a number of late chances and had a solid penalty appeal turned down before their hopes were killed off once and for all when Lima converted from the spot with the last kick of the match.
You can read how an eventful night of Europa League action unfolded with Sports Mole's live coverage of the match below.
5.30pmGood evening! Thank you very much for joining Sports Mole for our live coverage of the Europa League last 16 second leg clash between Benfica and Tottenham. The Premier League side have a mountain to climb tonight, so let's see if they have any chance of doing it...
5.32pmWe'll start with a look at our hosts tonight, who understandably enter this game as overwhelming favourites to progress through to the quarter-finals. Even ignoring their 3-1 victory in the away leg at White Hart Lane, Benfica's recent record - particularly at home - is hugely impressive and it would take a minor miracle for them to be knocked out tonight.
5.34pmBenfica currently lead the way in their domestic league and look destined to cruise to the title having opened up a seven-point lead over second-placed Sporting. That comes off the back of a remarkable run of 10 straight victories in all competitions and 25 games without defeat, 23 of which have resulted in wins. It must be noted that the Portuguese league is less competitive than the Premier League, but that is an impressive record in any league in the world.
5.36pmNo side has beaten Benfica since Olympiacos - who gave Manchester United so much trouble in their Champions League last 16 tie - managed to win against them way back on November 5. Things get even better for the Portuguese side when it comes to just home form as they have not been beaten in front of their own fans at all this season.
5.38pmIndeed, they have won 16 of their 19 matches at home this season and have not conceded a single goal in their last nine, scoring 20 in the process. The last time they conceded a goal at home was back on December 10 in a 2-1 win over French giants PSG.
5.40pmTo put such an impressive record down to a less competitive league would be doing a major disservice to Benfica, who have been just as good on the continental stage. Only Barcelona and Chelsea have won here in European competition since 2010, while they have not lost a single match here in the Europa League since the format change from the UEFA Cup. In that time, they have won 15 of their last 16 matches, drawing the other.
5.42pmThey were beaten finalists in last season's competition, and find themselves in it again this year having been knocked out of the Champions League group stages on goal difference. They finished just three point behind PSG and level with Olympiacos, but it was the Greek side who ousted them. Benfica came up against another Greek side, PAOK, in the round of 32 and made short work of them, winning 4-0 on aggregate to reach the last 16.
5.44pmAs for Spurs, things have turned very bad very quickly for manager Tim Sherwood. He appeared to be making steady progress as manager until the wheels came off in a 4-0 defeat to Chelsea earlier this month. His post-match rant suggested that he was beginning to feel the pressure, which subsequent touchline antics - such as the clash with Benfica boss Jorge Jesus in the first leg of this tie - have shown that his passions and emotions are in danger of getting the better of him.
5.46pmIt has been a tough period for the team, with three consecutive high-profile defeats causing questions to be raised over Sherwood's reign already. They were well beaten by Chelsea and Benfica, but they can take some solace from the fact that they played well - and arguably deserved to win - in the North London derby against Arsenal at the weekend. Of course, that means little when they go on to lose the match, but at least the performance showed some improvement.
5.48pmTheir form in general is pretty poor going into tonight's match, though. They have lost five of their last seven outings in all competitions, while they have only won once on the road in their last five away games. That victory was an impressive 4-0 win over Newcastle, but they have since lost three in a row without scoring a goal.
5.50pmTottenham's already impossible task gets even harder when you consider that Sherwood will be without a host of first team players through injury, as well as Vertonghen through suspension. He warned before the match that players would have to be played out of position, and that is the case with Sandro, who is forced to start at centre-back alongside Fryers.
5.52pmSpurs, quite simply, need a historic comeback this evening. Of course, they have already experienced one morale-boosting fightback in this competition this season, going 2-0 down on aggregate to Dnipro before scoring three goals in the second half of the second leg to eventually seal a 3-2 victory.
5.54pmElsewhere in the competition this season, Spurs have looked impressive. They cruised through their group with a 100% record, scoring the joint-most goals (15) and conceding the joint-fewest (2) of any of the teams in any of the groups. They will need to score at least three here tonight and, if they manage to pull it off, it will be one of their most memorable European nights.
5.55pmPREDICTION: We're nearing kickoff here in Lisbon, which means that it is time for my match prediction! Sorry Tottenham fans, but I simply can't see any way back for Spurs here. I would be surprised if they were to get a win of any kind, yet alone the comprehensive victory they need to progress. I'll go for a 2-0 win for Benfica.
5.57pmBENFICA STARTING XI: Oblak; M. Pereira, Luisao, Garay, Siqueira; Salvio, A. Gomes, R. Amorim, Sulejmani; Djuricic, Cardozo
5.59pmThere are three other Europa League last 16 ties taking place tonight, and I will keep you updated with major events from them as and when they happen. The pick of the bunch is undoubtedly Fiorentina vs Juventus, and I will be keeping a particularly close eye on events in that all-Italian clash tonight.
1 minKICKOFF: Benfica get us underway for this match, which should surely be a mere formality for them. Can they see out the tie or will Spurs launch a fightback?
3 minIncidentally, there is no Tim Sherwood on the touchline today. He is testing out a position in the stands to see whether he can judge the match better from there. Considering his history with Jorge Jesus and his outbursts on the touchline recently, that is probably a wise decision from the Spurs boss!
3 minSalvio makes an early burst forward from midfield right at the heart of the unfamiliar Tottenham defence. He is stopped in his tracks by a fine challenge from Danny Rose, however.
5 minSalvio has made a very bright start to this match. He makes another positive burst forward, nudging the ball past Rose before collecting it at the other side and sending a low cross into the box. However, there aren't many red shirts in the area and the cross is not great anyway as Sandro clears.
7 minSpurs are seeing a decent amount of the ball in the early stages, but they are yet to really threaten the Benfica defence. To stand any chance of pulling off a win tonight, you'd have to think that they'd go all-out attack from the off.
9 minCHANCE! Luisao fancies himself in front of goal against Spurs! Having scored two in the first leg he has the opening chance of the match here, latching on to Garay's header only to nod his own effort over the bar.
10 minYELLOW CARD! At the other end, Luisao goes into the book for a pull back on Soldado. It was a silly challenge and the referee was right to caution the big defender.
12 minSigurdsson bends the resulting free kick into the wall and it goes behind for a corner, which Benfica deal with comfortably. Still no joy in the final third for Spurs.
14 minNice football from Spurs as they inject a bit of pace into their attack. Rose played it inside to Soldado, who exchanged a flurry of one-touch passes with Chadli before the ball is put behind for a corner.
15 minCHANCE! The first Tottenham chance of the evening falls to Soldado, but he completely wastes it. The corner eventually falls to the striker after a deflection and he finds himself in plenty of space at the back post. He takes the ball down on his chest but then mis-hits his shot into the ground and wide of the near post. Poor from the Spaniard - that was a real opening.
17 minSpurs simply cannot afford to waste many chances this evening. They have made a decent start to the match without threatening that much, and they are unlikely to be given anything on a plate by Benfica, so they need to take whatever they get. An early goal could just sow the seeds of doubt in Benfica's mind.
19 minAmorim rises to compete for a header with two Tottenham players and lands very awkwardly, turning his ankle on the way down. He receives treatment but should be able to continue, which is fortunate because that one could have been nasty.
21 minVery dodgy moment for Sandro as a low ball comes into the six-yard box and he appears to panic and just nudges it back into the arms of the keeper. Friedel grabs on and, because it came off the thigh of Sandro, it is not a back-pass, but it could have easily ended up in the back of his own net. Signs of his lack of experience at centre-back.
22 minTownsend does well on the left flank, exchanging passes with Chadli before cutting onto his right foot and swinging a decent cross towards the back post. Lennon peels off his man but can only steer his header back into the middle, where Garay is waiting to clear.
24 minThe hosts are pretty comfortable at the moment, it must be said. Tottenham are not going gung-ho as they perhaps need to and it has been an even opening 25 minutes or so. Both teams have had a chance apiece, but neither keeper has been called into serious action thus far.
26 minCHANCE! Another sight of goal for Soldado, but this one is tougher. Luisao makes a mess of his clearance, allowing the ball to be nodded down to the Spanish striker inside the box. He has little time to sort his feet out, and his eventually shot takes a deflection on its way over the bar.
27 minThe resulting corner is swung into the middle and Chadli rises highest to meet it, only to glance his header wide. He climbed well there and will perhaps be disappointed that he couldn't make more of that opportunity.
29 minYou sense that Tottenham are not a million miles away from really threatening Benfica in this one. Their final ball needs to improve, but they look capable of making something happen and becoming the first team to score past Benfica at home since December 10.
31 minA fine raking pass finds Pereira scampering down the wing and he produces a good touch before sliding the ball into a good position in the area. Sandro does well to get in front of his man, however, before clearing the danger.
33 minThat has to go down as a waste for Spurs. They have a free kick in a really good crossing position, but Sigurdsson chooses to play it short for Townsend, who tries to drill a low ball into the box himself. It is easily defended and allows Benfica to launch a counter which eventually results in a corner.
34 minGOAL! Benfica 1-0 Tottenham Hotspur (Ezequiel Garay)
34 minThere is the opening goal for the hosts to give them a 4-1 lead on aggregate, and again it is a defender who has got it. Salvio skipped past Townsend all too easily before clipping in a nice cross for Garay to attack, and he did just that, planting a good header past a helpless Friedel.
36 minIn truth, that goal has not changed Tottenham's objectives in this match. They needed three goals at least to stand any chance of going through, and they still need that. The only difference is that three unanswered strikes for the visitors would now only force extra time.
38 minGood run from Siqueira down the left and he is picked out by a simple long ball upfield. However, the Brazilian's touch lets him down and the ball just about runs out of play before he can squeeze a cross in. That was a waste of a good position for the hosts.
40 minGood defending from Garay as he recovers from a little stumble to make up ground on Lennon as he threatened to scamper away from the defender. He lunged in with a well-timed challenge and even won a throw for his side.
42 minIf Benfica looked comfortable with a 3-1 aggregate lead, they are cruising now. A little of the edge seems to have been taken off Tottenham's play since going behind and the hosts are now controlling possession and dictating the tempo of the match.
44 minNo chances to report in the last few minutes, and no signs of Tottenham grabbing a goal back before half time either. They are beginning to look resigned to their fate now.
6.52pmSo far, so good for the hosts. They take a 1-0 lead into the halfway stage on the night and now lead 4-1 on aggregate over a Spurs side who have not shown the urgency of a team that believe they can get back into this one. It has been a fairly even encounter all told, but Spurs will need a much better second half if they are to stand any chance of a remarkable comeback.
6.54pmThe goal came from Garay, who notched the third goal from a centre-back in this tie after Luisao's brace in the first leg. It was created by Salvio, who skipped past his man too easily before clipping an inviting ball into the box that Garay attacked and nodded past the keeper. It was a good finish and a good cross, but the build-up was all too easy from a Tottenham point of view.
6.56pmSpurs had actually being doing fairly well before the Benfica goal and could have found themselves in the lead had Soldado taken a couple of chances that fell his way. The first was the best of the lot as he had time and space inside the box, but he fluffed his volley wide of the near post. He had two teammates waiting for a tap-in had he passed it across the box, but he can't blame him for going for goal himself. What you can blame him for is wasting a good chance to give his side an early lead.
6.58pmSoldado's next chance was a bit tougher, but one he may have made more of had he been in form. The ball again fell to him inside the box, but he chose to take a touch, allowing the defence to close him down and deflect his shot over the bar. A more instinctive first-time effort may have been a better option, and had he been performing better recently then he may well have done exactly that.
7pmOther than their goal, Benfica's best chance came when Garay nodded the ball to Luisao, but the Brazilian could not get his third of the tie as he nodded an effort over the bar. It has been comfortable for the hosts so far, and it is hard to see how they will be pushed much harder in the second half.
46 minKICKOFF: The second half gets underway as Tottenham kick us off again. They surely have no chance of overhauling the 4-1 deficit now and will want this 45 minutes to pass as quickly as possible.
48 minTottenham have not lost four games in a row for 10 years, but it is looking increasingly likely that that will be the case tonight. If they can get back to level pegging on the night, that would have to go down as a very good result, and that will be their main aim now.
50 minLovely football from Salvio as he advances into the box before rolling the ball under his foot and playing a delightful little pass inside the full-back for Pereira, who wins a corner. Salvio has been very impressive tonight.
51 minAlmost brilliant again from the hosts as Sulejmani plays a one-two with Luisao but just can't get the return pass under control when he would have been in a very good position.
53 minIt has been a bright start to this second half from Benfica as they look for a second that would kill the game off as well as adding extra gloss to the tie. They aren't committing too many men forward, but they aren't exactly sitting back on their lead either.
55 minSherwood's mind must be wandering as to whether or not he should make a couple of changes soon. This would be valuable experience for some of the youngsters on the bench and would also protect the few fit first team players he has left against further injury.
56 minCLOSE! Chadli does well on the left before playing an inswinging cross into the box that Sigurdsson is a whisker away from connecting with. It just moves beyond his outstretched boot, however, before rolling through to the keeper.
58 minThose defenders really are causing problems for Spurs. Another corner comes in and Luisao climbs really well to beat Chadli in the air, but he can't steer his header on target.
59 minCLOSE! Much better from Spurs. Townsend controls a long ball beautifully on the left before cutting inside and looking to drill a low shot in the bottom corner. It takes a touch on the way through before rippling the side-netting, although the keeper looked to have it covered anyway.
61 minUPDATE: Things are well and truly over in Spain. Valencia have taken a 1-0 lead over Ludogorets to make it 4-0 in aggregate to the Spanish side.
63 minUPDATE: Plzen have turned things around on the night against Lyon with two goals in quick succession to take a 2-1 lead. It is unlikely to have much of an impact on the final aggregate score, but it would be a big scalp for Plzen.
65 minStill no chances to report from the Stadium of Light in the last few moments. Tottenham are very much looking like a team trying to wind down the clock until they get to go home. They know this tie is beyond them now, and so do Benfica.
67 minDespite looking like this will be their fourth straight defeat, Sherwood can take some positives from the performance so far. Benfica have certainly not been playing at full throttle, but Spurs have matched them in a very difficult place to come so far.
69 minThis has been a good job well done by Benfica. They have dictated the tempo of the match and controlled the ball, particularly since taking the lead on the night. It has been a professional performance and they have done well not to become complacent.
71 minBENFICA SUB: The first change of the evening comes from the hosts as Djuricic is replaced by Enzo Perez.
72 minTOTTENHAM SUB: Spurs make a change of their own as Harry Kane comes on in place of Roberto Soldado. Once again it just hasn't happened for Soldado tonight.
73 minPerez is involved immediately as he gives the ball to Pereira, who sends a cross into the box. It is just about cleared to the edge of the area, where Siqueira hammers it well over the crossbar.
74 minSpurs come forward through Andros Townsend, who makes his way across the pitch before nudging the ball to Chadli. He moves it onto his right foot to curl an effort goalwards, but it is straight at the keeper and easy for him to collect.
76 minBENFICA SUB: The hosts make another change as Cardozo is replaced by Lima, who is the team's joint top scorer this season.
76 minTOTTENHAM SUB: Again, Spurs also make a change immediately afterwards, with Christian Eriksen coming on for Townsend.
78 minGOAL! Benfica 1-1 Tottenham Hotspur (Nacer Chadli)
78 minSpurs have something to shout about! Chadli once again makes his way to the edge of the box and moves it onto this right foot before hammering a low effort past the keeper at his near post. It was right in the corner, but there was enough power on it for it to beat Olbak.
79 minGOAL! Benfica 1-2 Tottenham Hotspur (Nacer Chadli)
79 minHold on? Spurs get a second in as many minutes and suddenly they have a real chance of turning this one around! Lennon stands a fine ball up into the box that Kane nods down to Chadli, who lashes the ball into the top corner on the turn. Tottenham are now a goal away from extra time - can they do it?!
81 minCHANCE! Another chance for Spurs to get a third goal! The ball is slipped through for Lennon to chase and his pace gets him to the ball before the keeper. He plays it inside, but Luisao is well placed to make a vital clearance into the arms of his own keeper with Sigurdsson in close attendance. We have a real game on our hands now!
83 minJust where has this fightback come from? The game looked for all the world as if it was drifting out into a 1-0 win for the hosts, but now Spurs have everything to fight for. This realy would be a remarkable comeback if Spurs can find one more goal.
85 minSuddenly, the Benfica players are looking to waste time at every available opportunity. They are getting nervous now as what looked like being a routine victory has turned into a desperate attempt to hold on to their slender advantage.
86 minBenfica threaten to get a second that would surely kill the tie off as Salvio goes for goal with a half volley, but Friedel is able to gather.
88 minUPDATE: Another Englishman who is making headlines in Europe tonight is referee Howard Webb, who has shown a red card to Gonzalo Rodriguez of Fiorentina. Andrea Pirlo scored the resulting free kick, giving Juventus a 1-0 lead that, as things stand, would put them through.
88 minPENALTY CLAIM! Spurs have a big penalty shout as they hound the defence into a mistake that Kane pounces upon. He has got the wrong side of Sulejmani, who appears to shove him in the back. The youngster goes down but the referee waves away the claims. I have certainly seen them given!
90 minYELLOW CARD! Perez goes into the book for a blatant body check on Aaron Lennon, which means that he will miss the next match through suspension. As things stand, that will be the quarter-finals.
90+1 minSpurs have three minutes of added time to change that. Can they complete a memorable comeback?
90+2 minCHANCE! Oh what a chance for Spurs to get a third goal! Sigurdsson pulls off his man inside the box to latch on to a diagonal ball, but his cushioned header is well saved by the keeper. Vital stop.
90+2 minBENFICA SUB: The hosts make another change as Sulejmani comes off for Markovic.
90+3 minCHANCE! Another huge chance for Spurs to level things up on aggregate as Kane has a clear header from close range. However, he can't generate the power to beat the keeper, who makes the save.
90+5 minWell, what a dramatic finale to the match! Benfica avoid defeat on the night with a penalty as the last kick of the game. It was a definite spot kick as Sandro brought down Lima in the box in a hurried attempt to win the ball back. Lima took the kick himself and made no mistake, sending Friedel the wrong way to secure a draw and a 5-3 victory on aggregate.
7.56pmIt could have been so much better for the visitors, however. They squandered a couple of good chances in the first half, but the best openings came late on with headers for Sigurdsson and Kane, both of which the keeper saved. They also had a very strong penalty shout turned down by the ref and, while the one they gave away late on was a certainly the right decision, Spurs fans will be bemoaning the fact that the ref didn't make the same decision just a few minutes earlier.
7.58pmBenfica appeared to be cruising into the quarters when Garay gave them the lead in the first half, and for a long time Spurs' second-half performance suggested that they thought that was the case too. However, two goals in as many minutes from Nacer Chadli turned the tie on its head and suddenly Spurs had something to fight for in the closing stages. They so nearly pulled off a remarkable comeback, but Benfica just managed to hold out in the end.
8pmRight, I'm afraid that is all we have time for this evening! Thank you very much for joining Sports Mole for what was a dramatic night in Lisbon as Spurs almost pulled off a seemingly impossible task. Their European dream is ultimately over, however, and it is Benfica who go through to the last eight thanks to a 5-3 aggregate victory. I will leave you with our match report and be sure to stick around for reaction and the day;s later Europa League kickoffs. From me, though, it is goodbye for now!