10 Memorable UEFA Champions League Last 16 Ties

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Claps hands Tony Stark style circa ending of Iron Man 3 (Just go with it, okay!), it’s February. Yup, the second month of the year, when we enter crunch time in the football season. When managers who haven’t been sacked announce that they’ll leave at the end of the season, and when UEFA Champions League football returns.

The time when, as ITV commentator Clive Tydesley said, ‘the Champions League becomes the European Cup again’, as the knockout football takes centre stage. And there have been some rather tasty ties in the first knockout round over the years, so, with one eye on next week’s resumption, here’s 10 of the classic match-ups in this round:

Porto v Manchester United (2004)

Rather fitting that we begin with the tie in which Tydesley gives his ‘European cup’ quote, as Manchester United, having toped their group with little fuss, met in the last 16, a Porto team that narrowly escaped the group phase, and their up and coming manager Jose Mourinho (the good old days then) had a chance to pit his wits against the mighty Red Devils and Sir Alex Ferguson.

It was no gain saying United were favourites, and midway through the first period Quinton Fortune would give them the lead. But two goals from Fortune’s fellow South African Benni McCarthy, one in the first period, and the other in the second, meant Porto would take a 2-1 lead to Old Trafford in a fortnight, a game where United would be without captain Roy Keane, who was sent off at the Dragao, much to Fergie’s incandescence.

United were still favourites to go through nevertheless, and in the first half of the second leg, Paul Scholes would give them the lead, and the midfielder was unlucky to see the offside wrongly deny him a second. It stayed at 1-0 for most of the game, United as it stood would go through on away goals, until the last minute, when Dmitry Alenichev was fouled just outside the United box. McCarthy’s free-kick was pushed away by Tim Howard, but Costinha was on hand to turn home the equaliser, sparking Mourinho’s famous touchline run at Old Trafford. Porto would go on to win the tournament, and some 14 years later, Mourinho is now the home manager at the Theatre of Dreams.

Chelsea v Barcelona (2005)

Well, Mourinho again. Clive Tydesley again. After his European triumph (or triumphs) with Porto, Jose left for Chelsea, where he got tagged the ‘Special One’. The Blues were top of the Premiership and flying, while Barcelona were also ahead of the rest in La Liga when both sides clashed at the Camp Nou in the first leg. Chelsea took the lead through a Juliano Belletti own goal, an advantage they would take to halftime. But things took a big swing in the second period, when Didier Drogba was sent off for his lunge on Barcelona goalkeeper Victor Valdes. The hosts pressed home their numerical advantage, as two goals in five from Maxi Lopez and Samuel Eto’o meant they would go into the second leg ahead.

But the Blaugrana would be caught unawares and left shell-shocked after 19 minutes of the return leg, as Eidur Gudjohnsen, Frank Lampard and Damien Duff all got on the score sheet to give Chelsea a three-goal lead on the night (4-2 on aggregate). Barcelona were left reeling, and in need of a lifeline, which they got after Paulo Ferreira’s handball in the Chelsea box enabled Ronaldinho to score a penalty, one which Petr Cech came close to saving. But Cech could do nothing about what happened just before halftime, as an outrageous Ronaldinho toe-poke from the edge of the box put the scoreline at 3-2, and Barcelona ahead on away goals. Chances would fly at both ends in the second half, Eto’o guilty of missing one, while Joe Cole also fluffed his lines for Chelsea. But the Blues would get back in the aggregate lead with 12 minutes left, John Terry heading home Lampard’s corner to put them within touching distance of the last eight. Barcelona sought another reply, but found none, and for the first time since the competition was renamed, no Spanish side would be in the quarter finals. For Chelsea, it was delight, as Mourinho joined the players’ celebrations after the final whistle, as Clive Tydesley declared that who could stop the Blues from European glory. The answer came in semi-finals, in the form of a familiar face in Liverpool.

Werder Bremen v Juventus (2006)

Werder Bremen had made history in the group stages, as they became the first side to lose their first three games and still qualify for the knockout phase, and in this round of 16 tie they struck first, Christian Schulz giving them the lead at home Juventus. But the Old Lady turned things around, and goals from Pavel Nedved and David Trezeguet had them leading with eight minutes left. Bremen, though, showed the resolve they demonstrated in their group, and late strikes from Tim Borowski and Johan Micoud gave them a first leg advantage.

That advantage was doubled 13 minutes into the second leg, Micoud again the scorer, as Bremen started to dream of the last eight. Trezeguet grabbed an equaliser in the 65th minute, but Fabio Capello’s side needed one more to go through. It didn’t seem forthcoming, Juve seemed stuck and on the verge of elimination, until Bremen’s goalie Tim Wiese caught a corner in the 88th minute, and his histrionic roll led to the ball slipping out of his hands and into the path of a grateful Emerson, who rolled the ball into an unguarded net, and rolled the Bianconeri into the next round, much to Wiese’s horror.

Real Madrid v Bayern Munich (2007)

It was the resumption of the international rivalry between Real Madrid and Bayern Munich, as they were pitted together for the fourth time in seven years. Real had triumphed in two of the previous three, and were in mood to lay off here, Raul giving Los Blancos the lead after just 10 minutes. That lasted only 13 minutes, however, as Lucio’s header pulled Bayern Munich level, but Real would take a 3-1 lead into halftime, Raul adding his second before Ruud van Nistelrooy got on the score sheet himself. Bayern looked in real trouble in the tie, but gave themselves a huge lifeline with two minutes left, Mark van Bommel’s shot handing the Bavarians two away goals in a one-goal loss.

And they took advantage quite literally as the second leg begun, an error from Roberto Carlos led to Roy Makaay scoring the fastest ever Champions League goal, and Real were chasing the game from the off. Bayern added another not long after the hour mark, Lucio repeating his first leg trick to give Los Blancos a mountain to climb. Van Nistelrooy would pull one back from the penalty spot in the 83rd minute, but they would have a goal disallowed after, Sergio Ramos the guilty party, as they bowed out of the competition at this stage for the third year running.

Fenerbahce v Sevilla (2008)

It was uncharted territory for Fenerbahce in 2008, as Sari Kanaryalar, under Brazilian manager Zico, negotiated a group involving Inter Milan, PSV and CSKA Moscow for a berth in the last 16. The Turks had been making an impression in the competition, and against Sevilla, backed by a raucous Sukru Sarakoglu crowd, took a 17th-minute lead through Mateja Kezman. Sevilla had also been impressive themselves, beating Arsenal to top spot in Group H, and levelled just six minutes after through Edu Dracena’s own goal. Fenerbahce went again and retook the lead, Diego Lugano’s thumping header just before the hour mark sending the home crowd to cacophony once again, but once again Sevilla wouldn’t lie down, and Julien Escude dragged them level again, 10 minutes after Lugano’s moment. The hosts, though, ensured they would finish with a first leg advantage, as substitute Semih Senturk grabbed a winner three minutes from time.

The second leg was just as action-packed, and less than 10 minutes had been played when Sevilla scored twice, a brilliant Dani Alves free-kick and a Seydou Keita thunderbolt put them on course for the last eight, then Frederic Kanoute added a third for the hosts, after Deivid pulled one back for Fenerbahce. But Fenerbahce and Deivid weren’t about to throw in the towel, and the Brazilian scored his and his side’s second with 10 minutes left, to force extra-time.

No goals came in the extra half-hour of football, which meant the tie would be decided by penalties. The first kicks of both sides- Kanoute and Wederson- were successful, but next weren’t, as Escude and Edu both missed. Ivica Dragutinovic and Mehmet Aurelio both scored to make it 2-2 in the shootout with three played each, but Sevilla’s next takers would fail, as Enzo Maresca and Alves were both denied by Volkan Demirel, either side of Kezman scoring, to send the Turks into their first ever Champions League quarter-final.

Real Madrid v Liverpool (2009)

Real Madrid had lost in four successive last 16 ties coming into this, they hadn’t had the best season so far, already dismissing Bernd Schuster and hired Juande Ramos, and for some reason, signed Julien Faubert on loan from West Ham (old, but still shockingly gold). Liverpool, meanwhile, had reached at least the semis in three of the last four seasons, and were locked in a title race in the Premier League. The Reds took a deserved 1-0 win in the first leg, thanks to a late header from Yossi Benayoun, and were in the driving as Real came to Anfield for the return.

Back in Merseyside, Liverpool went guns blazing, and by halftime they were two up (three on aggregate), Fernando Torres and Steven Gerrard (from the penalty spot) putting them within touching distance of the next round. Gerrard added another with a lovely side-foot finish just a minute after the break, before Andrea Dossena put the gloss on the win. 4-0 on the night, 5-0 on aggregate, yet it was proof of how much more it could have been to recognise that Real Madrid goalkeeper Iker Casillas had a very good game.

Milan v Barcelona (2013)

When the draw for this tie was made, it looked a no-brainer, Milan had been less than impressive all season, and had the deficiency of Zenit St. Petersburg to thank for making it this far, while Barcelona had lost just twice all season before this first leg. But the Rossoneri produced a performance worthy of the tales of Catenaccio, defending superbly and took the lead just after halftime through Kevin Prince Boateng, and that lead was doubled late on by Sulley Muntari to give Milan a first leg advantage.

Barcelona knew they had a job on their hands in the second leg, no team had ever lost a first leg by two goals without scoring and qualified. But they got off to the perfect start at the Camp Nou, thanks to none other Lionel Messi, and the deficit was halved after four minutes. Barcelona rode their luck towards the end of the half, as M’baye Niang broke free one-on-one with Victor Valdes, only to hit the post, and right away, straight down the other end, Messi added a second, and the scores were level on aggregate with three-quarters of the tie played. Barcelona began the second period as they did the first, and David Villa made it 3-0 on the night, and 3-2 on aggregate, before Jordi Alba added a fourth in stoppage time to seal the tie. History was made, and a precedent was sent for some four years later.

Sevilla v Leicester (2017)

Leicester had defied football logic to win the Premier League in 2016, and transferred their fairy-tale powers to Europe, to advance to the first knockout phase of this competition last season. Opponents Sevilla were seeking a first quarter-final appearance and dominated the first leg, Pablo Sarabia and Joaquin Correa scoring to put them in control. But the Rojilblancos had missed a penalty much earlier in the game, and late on Jamie Vardy pulled one back for Leicester, an away goal to take back to the King Power.

By the second leg three weeks after, Leicester were lining up with a new manager, Claudio Ranieri had been sacked after the first leg loss, and was replaced by assistant Craig Shakespeare. The Foxes had won their first two domestic games under the new manager, and took the lead here through skipper Wes Morgan. Leicester were now level in the tie, and ahead on away goals, but they would take an outright lead in the second half, through Marc Albrighton. Sevilla, despite being reduced to 10 men after Samir Nasri saw red, had a chance to level on aggregate after Franco Vazquez was fouled in the box by Kasper Schmeichel, but, like the first leg, the penalty was spurned, Steven Nzonzi the guilty party this time, his week effort saved by Schmeichel, and Leicester held on for a heroic win, and a place in the Champions League quarter finals, less than 10 years playing in the English Third Division.

Manchester City v Monaco (2017)

There weren’t many ties as anticipated as this one when the draw was made back in December 2016, as it pitted Manchester City, a side with a manager that prides on attacking football, against Monaco, a youthful storming through the French first division and had amassed 100 goals by February 2017.  It was City who made the early inroads in the tie, and took the lead through Raheem Sterling, but goals from Radamel Falcao and teenage forward Kylian Mbappe ensured Monaco would go into the break in the lead. Falcao missed a penalty at the start of the second half, but made amends with an impudent chip, not long after Sergio Aguero had pulled City level. Aguero would restore parity once more with a well-taken volley, before goals from John Stones and Leroy Sane gave City a 5-3 first leg win.

Prior to the second leg, city manager Pep Guardiola had emphasised Monaco’s attacking prowess, and therefore the need for his side to score at Stade Louis II, and so named an attacking line-up. It didn’t quite work out for the visitors though, and by the half-hour they were deservedly two down, Mbappe and Fabinho with the goals that put Monaco ahead in the tie. City improved in the second half, and with 20 minutes left, Sane pounced on Danijel Subasic’s save from Sterling to make 2-1 to Monaco on the night, but 6-5 to City on aggregate. City were back in the driving seat, but Monaco weren’t done yet, and from Thomas Lemar’s free-kick, Tiemoue Bakayoko got in front of Aleksandar Kolarov to guide in the header. There would be no more goals, as Monaco went through on away goals after a 6-6 aggregate scoreline, on their way to an impressive semi-final achievement.

PSG v Barcelona (2017)

Of course. Perhaps the greatest ever Champions League last 16 tie, one that’s still fresh in the mind, and will live long in the memory. Both sides had been having under-par campaigns, and were on course to relinquish their domestic titles, but PSG were in a more questionable state, and Barcelona were still regarded as favourites for the European title. On the evidence of the first leg though, it was nothing like that, Le Parisiens had a night to remember on Valentine’s, outplaying, outthinking and outmuscling Barcelona, by halftime goals from Angel Di Maria and Julian Draxler had them 2-0 up. They would add two more after the break, Di Maria getting his second, and Edinson Cavani wrapping things up. Surely the tie was over.

There was still a second leg to be played, but Barcelona had a lot of ground to make up, and no team had ever erased a four-goal first leg deficit. But they got off to a flyer, Luis Suarez pouncing on some uncertainty from PSG goalie Kevin Trapp to put Barca ahead on the night, and by halftime they were halfway to the comeback, Layvin Kurzawa’s own goal making it 2-0 on the night. Luis Enrique’s side began the second half as they did the first, and following a Thomas Meunier ‘foul’ on Neymar (yes, this column is still bitter and thinks it wasn’t one), Lionel Messi stepped up to make it 4-3 on aggregate. Barcelona had the wind in their sails, but things would take a different shape soon after, as Cavani made it 3-1 on the night, 5-3 on aggregate, and had Barca needing three more goals. The home crowd were deflated, and only some profligacy from Di Maria and Cavani prevented PSG adding more goals, the tie seemed over. But in the 88th minute, Neymar curled home a free-kick, then Luis Suarez was supposedly fouled by Marquinhos (again, still bitter), and Neymar converted the penalty in stoppage time. Now it was 5-5 on aggregate, but PSG were ahead on away goals, until the last minute, when Neymar’s cross into the box was turned home by Sergi Roberto, sparking mayhem across the pitch, the dugout, stands, commentary boxes and broadcast studios as well. Barcelona had done the impossible and erased a four-goal deficit. It was the kind of turnaround that makes one think their names were already written on the title for 2017, not to be knocked out in the next round by Juventus, although it was the latter that happened. 

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