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The draw for the last 16 of the Champions League always promised to throw up some mouth-watering match-ups – and it did not disappoint in that regard.<a href="https://www.goal.com/en/news/champions-league-last-16-draw-liverpool-real-madrid-man-city-leipzig-chelsea-dortmund/bltb93c2653b57ed6c6" target="_blank">Reigning champions Real Madrid will take on the side they beat to claim the trophy in Paris last May, Liverpool, while Bayern Munich will meet Paris Saint-Germain in a repeat of the 2020 final.</a> Man City fared far better, with the favourites paired with RB Leipzig, while Napoli will also be pleased, having drawn Eintracht Frankfurt. <script type="application/json" data-placement="fcplayer-semantic">{"type":"fcplayer-semantic","data":{"embedCode":"//cdn.fcp.codes/embed-code-template/embed-code-template.js#SEMANTIC_5704afb8-c10b-4ba5-9cb4-d7fb6098ef90"}}</script>Below, GOAL runs through all of the winners and losers from a fascinating last-16 draw...

More Madrid misery for Liverpool? Winners and losers from the Champions League last 16 draw as PSG are punished with Bayern pairing

As it stands, this will be Pep Guardiola's last season at Manchester City. His contract expires next summer and it remains to be seen if he will sign a new one, which is <a href="https://www.goal.com/en/news/guardiola-new-manchester-city-contract/blt40e5598aa826962e" target="_blank">a real cause for concern for the club's supporters, who understandably fear an era of unprecedented success will end the moment the Catalan leaves.</a>Still, even if Guardiola does depart at the end of the 2022-23 campaign, there's every chance he would do so after finally winning a Champions League with City. Their prospects have certainly been boosted by the draw for the last 16.Guardiola, of course, knows all about the quality of RB Leipzig. Christopher Nkunku scored a hat-trick at the Etihad in last season's group stage, and he struck again when the Germans beat City 2-1 at the Red Bull Arena on matchday six. However, there is no getting away from the fact that Leipzig represent an excellent draw for City, who could have been paired with the likes of AC Milan, Inter or PSG.Guardiola's side should have far too much creativity and firepower for a team currently sitting sixth in the Bundesliga standings.Expect City to cruise into the quarter-finals while two of their four biggest rivals for the title (Madrid, Liverpool, PSG and Bayern) fall by the wayside.

WINNER: Pep Guardiola 

Jurgen Klopp would surely have been hoping for anyone but Real Madrid. Liverpool have endured nothing but misery every time they've faced the Spanish side during his Anfield reign. A resurgent Mohamed Salah may well be looking forward to another chance to avenge the injury he sustained in the Champions League final loss to Los Blancos in 2018, but history is most certainly against his team. Liverpool may have beaten Madrid in the 1981 European Cup decider, and knocked them out of the last 16 in 2008-09, but the reigning Liga champions have got the better of Klopp's Reds every time they've met.There was Loris Karius horror show in Kyiv, a 3-1 aggregate win in the 2020-21 quarter-finals, and, of course, a 1-0 victory in Paris in May that owed much to the brilliance of Thibaut Courtois. There are signs that Liverpool are improving after a dire start to their Premier League campaign and they should have some key players back by the time the last 16 rolls around. It's also worth pointing out that Europe has proven something of a safe space for them in recent weeks, as underlined by last week's win over Napoli, but they have paid a heavy price for failing to pip the Partenopei to top spot in Group A. Klopp and his players may be 'mentality monsters' but they will have nothing but bad memories of Madrid.

LOSER: Liverpool

Club Brugge were undoubtedly the side that every top seed wanted in the draw – and Benfica got them.Nobody could begrudge the Portuguese side their good fortune either. They deserved it after eliminating Juventus and then taking top spot away from PSG by the narrowest of margins, and in the most dramatic fashion. Indeed, <a href="https://www.goal.com/en/lists/champions-league-winners-losers-benfica-psg-simeone-european-exit/blt5e0cf390ccf864dd" target="_blank">Joao Mario's 92nd-minute strike against Maccabi Haifa could prove one of the defining moments of this season's Champions League.</a> It resulted in two European heavyweights being pitted against one another in the last 16. Benfica have their own campaign to worry about, though, and they will now be supremely confident of reaching the quarter-finals for the second consecutive season. Brugge should not be underestimated, of course. They qualified for the knockout stage by winning their first four games, and without conceding a goal.However, they still ended up finishing as runners-up in Group B to a Porto side that an undefeated Benfica currently lead in the Primeira Liga by eight points.

WINNER: Benfica

Paris Saint-Germain's players didn't know Benfica were running riot against Maccabi Haifa last Wednesday evening. They thought victory over Juventus would be enough to seal top spot in Group H."They tried to warn us," <a href="https://www.goal.com/en/news/mbappe-laments-lack-of-warning-psg-stars-losing-top-spot-champions-league-group/blt460c435a8f37f853" target="_blank">Kylian Mbappe revealed to RMC Sport</a>. "But only at the end."And by that stage, it was too late. A relentless Benfica had secured a 6-1 win that changed everything.PSG had finished dead level with the Eagles on points, goals scored and goals conceded, while their head-to-head record was identical. But it was the Portuguese who progressed as group winners by virtue of having scored more goals away from home.Mbappe was upbeat. "It doesn't matter," he argued. "We qualified."But PSG were already through when they touched down in Turin. First spot was the primary objective, and they blew it by not keeping their players abreast of what was happening in Haifa.Now, the Ligue 1 leaders must face Bayern Munich, who emerged from a group containing Inter and Barcelona with a 100 per cent winning record. PSG have no reason to fear any side, of course. They have Lionel Messi, Neymar and Mbappe up front. However, their quest to win a first Champions League has been made a whole lot more difficult by an avoidable breakdown in communication.

LOSER: PSG

Italian football remains beset by financial and structural problems, which makes the performance of the nation's representatives in this season's Champions League all the more remarkable. Juventus were obviously an embarrassment, even losing to Maccabi Haifa during a woeful group-stage campaign that saw them eliminated with a round to go. However, for once, their compatriots stepped up to the mark. Inter caused a huge upset by getting the better of Barcelona to progress as runners-up to a dominant Bayern in Group C, while Milan maintained their upward trajectory, recovering from last year's first-round exit by accompanying Chelsea into the knockout stage. The big story, though, was Napoli, who became the toast of Europe by kicking off their campaign with a thrilling demolition job on Liverpool and then storming into the last 16 with five consecutive wins, wowing all and sundry along the way with some fantastic football. The good news is that this unexpected Serie A resurgence could continue into the quarters. Napoli avoided one of the massive second seeds by drawing Eintracht Frankfurt, while Inter and Milan both got off lightly, given they were in Pot 2. The Nerazzurri's league form has been horribly patchy this season but they will seriously fancy their chances against Porto, while Milan will be cautiously optimistic of defeating Antonio Conte's Tottenham, who have a nasty habit of underperforming against every big team they come across.

WINNER: Serie A sides

More Madrid misery for Liverpool? Winners and losers from the Champions League last 16 draw as PSG are punished with Bayern pairing | Goal.com Tanzania

The draw for the last 16 of the Champions League means Liverpool could suffer more misery against Real Madrid, while Paris Saint-Germain have been punished for failing to finish top of their group after being paired with Bayern Munich