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Firsts are not easy to come by for Jose Mourinho at this stage of his long, often highly dramatic, career.

But on Wednesday night in Lisbon, Anatoly Trubin provided such a moment.

Simply beating 15-time European champions Real Madrid was not going to be enough for Benfica.

In added time to added time, they led 3-2 but needed another goal or their Champions League campaign would be over.

A free-kick provided them with one last chance and goalkeeper Trubin was sent forward.

Moments later it was pandemonium at Estadio da Luz with Benfica players running in all directions and Trubin ending his own euphoric wild charge with a knee slide having scored the decisive goal with a bullet header.

“A fantastic goal, a historic goal, a goal that nearly brought the whole stadium down – and I think it was very deserved for us,” Mourinho said.

“For Benfica it’s an incredible prestige to beat Real Madrid.”

Given the way the league format works with 18 games taking place simultaneously on the final matchday, it is little wonder Trubin was not fully aware of what his side needed.

They were heading out on goal difference at the end of the eight-round league phase, until his sensational intervention. Marseille were the unlucky side, falling out of the play-off places as Benfica snatched their spot.

A couple of minutes before his goal, Trubin had dropped to his knees after claiming a cross, seemingly trying to waste a few seconds to close out the win, unaware Benfica were still going out as it stood.

“Before, I didn’t understand what we needed,” Trubin said. “I see everyone start to point at me and I go and after I see [I can go forward]. We need one more goal.

“I don’t know, I don’t know what to say. A crazy moment.

Settling in has not been straightforward for Mourinho since returning to Benfica in September.

There was already a degree of scepticism when ‘The Special One’ was appointed, some 25 years after his first – very brief – spell at the club, and a feeling that the 63-year-old was well past his peak.

Four and a half months on, Benfica remain unbeaten in the league but sit third, 10 points behind leaders Porto who have taken 55 points from a possible 57. The chances of Mourinho adding a ninth league title to his collection look slim in the extreme.

Meanwhile, in Europe, they lost their first four games of the league phase and even wins over Ajax and Napoli did not look like being enough after a loss in the penultimate round of fixtures.

His side also exited the domestic cup with a quarter-final loss at Porto, where Mourinho made his name more than 20 years ago.

As it turned out, that game on 14 January provided Trubin with a trial run for his Champions League heroics.

“We knew he could do it,” Mourinho told Uefa. “In the game at the Dragao, Trubin was also there in the final action and headed it but a Porto player blocked it.”

The Ukrainian would not be denied this time, a perfectly timed run and superb header bringing Benfica back from the brink to keep their European hopes alive.

“It’s massive for Mourinho, because everything hasn’t really worked out for him since taking over from Bruno Lage back in September,” European football expert Julien Laurens said on BBC UCL Match of the Day.

“To win tonight in that way, the narrative was there. Against Real Madrid his former club, against [Madrid coach Alvaro] Arbeloa who he is the mentor of and he considers him as his son, him on the other bench.

For Mourinho, beating Madrid ranks as a result to treasure.

“To win against Real Madrid carries importance and is significant. In that moment we had to give it everything,” Mourinho said.

The former Chelsea boss spent three seasons at the Bernabeu between 2010 and 2013, going head to head with Pep Guardiola’s mighty Barcelona – and coming out on top to win La Liga in 2011-12.

Guardiola was alert to how the latest chapter of the Mourinho story unfolded, with he and his Manchester City players eager for Benfica to cling on for a victory that ensured the Premier League side finished in the top eight.

“We didn’t know Benfica needed a goal to qualify, so when the goalkeeper goes up, we say, ‘why you go?’, because Madrid can equalise and we are out,” Guardiola said after City’s win against Galatasaray.

“But it was a good strategy for Jose to score the fourth goal, right!”

Another battle with Guardiola may have to wait, but having just claimed his first win over Los Blancos, there is a good chance Mourinho will get the opportunity to get a second in February.

With Arbeloa’s side finishing ninth in the league phase and Benfica in 24th, there is a 50% chance they will meet in the play-off round.

The other side Benfica could face? Inter Milan, with whom Mourinho won the Champions League as part of a famous treble in 2010.

“I can’t say I prefer one or the other because going to Madrid I like a lot and I’ve not gone there; to go to Milan I like a lot and I don’t go there either,” Mourinho said.

Whoever Benfica draw, few would rule out Mourinho masterminding something special at the Bernabeu or San Siro.

Liam Rosenior might have downplayed the significance of Chelsea’s win against Antonio Conte’s Napoli in the Champions League after a comeback victory that secured a place in the last 16.

But outmanoeuvring a manager who once occupied his office at Stamford Bridge and guided them to the Premier League title should rank high among the new Blues manager’s career achievements.

Managing in the Champions League for only the second time after taking charge of the club earlier this month, Rosenior was the novice facing a master tactician whose legacy looms large over the club.

With Chelsea 2-1 down in the hostile Naples atmosphere, they were facing the prospect of having to go through the two-legged play-offs to keep themselves alive in the competition.

But the 41-year-old English manager’s proactive tactical switches in the second half sparked a stunning Chelsea comeback with Joao Pedro scoring twice to secure a top-eight finish.

“It’s not about me,” Rosenior said after Chelsea became only the second team to defeat Napoli on home soil in 21 matches.

“My job is to win games here as the manager of Chelsea, so it’s not about where does it rate in my career. I’m not really fussed.”

While Rosenior and Chelsea celebrated securing a direct spot in the last 16 with victory at the Stadio Diego Armando Maradona, Conte was left staring into a familiar abyss at full-time.

The result in Naples could prove to be of great importance for Rosenior whose appointment in place of Enzo Maresca was hardly greeted with open arms.

Rosenior’s lack of elite experience – having moved from sister club Strasbourg after stints with Derby County and Hull City in the Championship – saw him labelled by some as a ‘yes man’.

He also experienced the wrath of the fans who voiced anti-ownership chants questioning the ambition of the BlueCo.

Rosenior has been adamant from the start that his reply must be through results.

And he has put together an impressive set of results in his first weeks with five wins in six matches and the latest over a former Chelsea favourite should win him the confidence of more supporters.

“These players lost a manager that they really respected for reasons that are beyond my control or knowledge,” Rosenior told TNT Sports.

“So when you go through that as a young group, to accept a new manager the way they have done and for them to work as hard as they have done is a credit to them.

“It’s not about me or my ego or trying to prove anything. I’m trying to do the very best I can with my group, with my staff and hopefully we can have more and more really good nights like this.”

Rosenior’s introduction of Cole Palmer at half-time provided assisted both of Joao Pedro’s goals while Trevoh Chalobah added defensive solidity after coming on later in the half as the Blues restricted Napoli to a single shot on target after the break.

The Chelsea manager added: “I’m learning all the time about my team, about what we’re capable of.

“I really wanted to be front-footed today. I wanted to go out and win the game.”

His impetus was rewarded with a win that helps Chelsea avoid adding a two-legged play-off to their already busy schedule.

“It’s massive – that is huge for us to be able to be able to work with the players on the training round,” Rosenior said.

Bigger challenges await Rosenior and his young squad as they enter the business end of the competition but the London-born coach is optimistic.

“You have to enjoy this job,” he said.

“We’re the luckiest people in the world to do this job. You have to enjoy these moments, but we want more.

Conte lifted the Champions League as a player in 1995-96 but has experienced nothing but despair as a manager in Europe’s premier club competition.

Wednesday was the 50th game the Italian has managed in the Champions League across spells at Napoli, Tottenham, Inter Milan, Chelsea and Juventus.

Conte has 17 wins, 17 defeats and 16 draws in those matches.

He has collected 61 points from 44 matches he has overseen in the group stage/league phase at an average of 1.39 points per game – a rate lower than his contemporaries Carlo Ancelotti, Massimiliano Allegri, Jose Mourinho and Pep Guardiola.

Meanwhile, he has managed 618 games across all other competitions, winning 374 and suffering only 110 defeats, collecting 2.03 points per game at a win rate of 60.5%.

His sides have been knocked out in the group stage four times, with only Jorge Jesus (five) experiencing more group-stage exits as manager since 2012-13, and the round of 16 twice.

A quarter-final exit with Juventus in his maiden adventure in the competition remains the best run he has managed, though he guided Inter to the Europa League final in 2019-20.

Potentially adding to his frustrations, both Juve and Inter reached Champions League finals within two seasons of him departing,

He has also failed to win the Coppa Italia despite a decade of dominating Serie A as a coach and an FA Cup with the Blues in 2018 remains his only cup triumph.

“It’s disappointing,” Conte said of the defeat.

“Chelsea were better in the final third, but the players had a good game. I wanted to stay in this competition. We’re proud nonetheless as we played well and deserved more.”

Watch highlights of every Champions League game from 22:00 on Wednesday on BBC iPlayer and the BBC Sport website and app.

Newcastle United have experienced all manner of emotions at the Parc des Princes.

It was here, just a couple of years ago, that Eddie Howe’s side were denied a famous win against Paris St-Germain after the hosts were awarded a controversial penalty in stoppage time.

That 1-1 draw left a bitter taste, as a result, but there was a very different feeling in the away dressing room on Wednesday night following the same result.

This was a night when Newcastle – not PSG – came from behind after putting in a gutsy showing against the Champions League holders.

There have been a number of occasions where these players and staff have approached the away end sheepishly this season following a poor display on the road.

This was not one of them.

“We love Newcastle, we do,” the travelling support sang at full-time.

The point was not enough to secure automatic qualification for the last 16, but Eddie Howe’s side look well placed to progress past Monaco or Qarabag if they build on this.

“We wanted to win tonight,” the Newcastle head coach said. “We didn’t want the extra games, but we will take it.

“We will go down that route and we are going down that route in the best possible way with a strong performance against the holders of the competition.

Yet it looked like history was about to repeat itself at one point.

The game had not long kicked off when PSG were awarded a controversial penalty following a video assistant referee (VAR) review after the ball bounced off the arm of Bradley Barcola and then struck Lewis Miley’s hand inside the box.

It brought back memories of when Newcastle defender Tino Livramento was penalised for an unintentional handball at the same stadium in 2023.

Kylian Mbappe took full advantage that night but, this time, Pope got a strong hand to Ousmane Dembele’s spot-kick to briefly quieten the Parc des Princes.

Although Vitinha did put the hosts in front, just a few minutes later, Newcastle did not crumble, even after such a shaky start.

They did not let their frustrations get the better of them, either, when they were not awarded a penalty of their own after the ball struck Marquinhos’ hand inside the box a few minutes before Joe Willock equalised.

Willock was one of five players recalled by Howe and this was a night when the Newcastle head coach’s faith in his squad eventually paid off.

With an eye on Saturday’s trip to Anfield, Howe made five changes as Dan Burn, Anthony Elanga, Jacob Ramsey, Willock and Nick Woltemade came into the team, knowing he needed fresh legs.

They certainly stepped up – not least Burn, who wore the captain’s armband.

Burn, making his first appearance since breaking a rib and puncturing a lung, was even named man of the match after a colossal performance.

To think the 33-year-old had been “anxious” before the game.

“That injury did shake me up a little bit,” he said. “It was something I had never had before.

“I was really happy when the first whistle went because I just settled back into my routine and didn’t think about it.

Then there was Willock.

The midfielder was subject to abhorrent racial abuse from an anonymous Instagram account last month, but he embodied his side’s resilience.

Indeed, after heading his side level, in first-half stoppage time, Willock defiantly put his finger to his lips as the home support whistled loudly.

“That was the Joe Willock of old,” Howe said. “Always a scorer of big goals. His goalscoring record when he first joined the club was really strong and he scored goals in my first year in particular so really pleased for him.

“He’s had a tough time with injuries. He’s trained really well for us behind the scenes. He’s been waiting for opportunities and today was the right time.”

It was Willock’s maiden goal in the Champions League.

But this is a competition these players now feel they belong in after so many of the squad only sampled life at Europe’s top table for the first time back in 2023.

Newcastle exited the group stage that year, but they have certainly relished the new format, finishing level on points with PSG in the standings.

Howe’s men have only lost two Champions League games – against Barcelona and Marseille – and swatted aside PSV Eindhoven, Benfica, Athletic Club and Union Saint-Gilloise.

Their European adventure continues.

“This is a really good step in the right direction,” Pope told TNT Sports. “I’m really pleased with that.

“There are things to work on. We came to this competition two years ago and didn’t get to this stage so this is really exciting for us.

The Premier League is flexing its muscles in Europe as five English teams finished in the top eight of the Champions League to reach the knockouts.

That could become six in the last 16 if Newcastle win their two-legged play-off after they finished 12th in the league phase following a 1-1 draw at defending champions PSG on Wednesday.

Arsenal finished in first place with Liverpool third, Tottenham fourth, Chelsea sixth and Manchester City finishing eighth.

History could be made if Newcastle progress through the play-offs as never before have there been six Premier League teams in the Champions League knockouts.

“That is dominant,” said Spurs boss Thomas Frank.

“I think we all said for a few years the Premier League is the best league in the world and I think this is another sign of it.”

The most obvious starting point is the financial power of the Premier League, which significantly outweighs other leagues.

Six Premier League sides sit inside the top 10 of the Deloitte Football Money League, while 50% of the top 30 come from the English top flight.

TV rights have generated enormous broadcast revenues for Premier League sides, with the income from that source dwarfing those of other countries.

Last summer, Premier League clubs outlaid more than ever before in the transfer window as spending surpassed £3bn.

More money means clubs can invest in bigger squads, with Arsenal seeing the benefits of spending big to increase their strength in depth as they finished first in the league phase of the Champions League and sit top of the Premier League.

“The biggest single reason that the English clubs have been dominant so far is the financial power of the Premier League,” former Liverpool defender Stephen Warnock told BBC Sport.

“Also, it is about how competitive they have got by fighting it out and being in and around each other – they have pushed each other on.”

Newcastle forward Anthony Gordon also says a more open style of play in Europe has benefited English teams, while the Premier League is “more physical than I’ve ever known it to be”.

“I think in the Champions League, teams are more open. They all try to play. It’s less transitional,” he added.

“It [the Premier League] is like a basketball game sometimes, it’s so relentless physically. There’s not much control, it’s a running game and sometimes it’s about duels, whoever wins the duels wins the game. Or moments.

“The Champions League is a bit more of an older style of game, more football based. Teams come and try and play proper football.

It is undoubtedly an impressive achievement for five – and potentially six – Premier League teams to reach the knockouts.

But was the fixture computer kinder for them than other teams?

At the start of the season, football data statisticians Opta analysed every team’s Champions League fixtures and ranked them all to work out who had the kindest draw.

Arsenal’s fixtures were ranked the third easiest, with Tottenham fourth, Liverpool seventh and Chelsea eighth.

The last – and only – time five Premier League teams made it through to the knockouts was in 2017, when Chelsea, Liverpool, Manchester City, Manchester United and Tottenham all progressed.

However just two of those sides – Liverpool and Manchester City – got beyond the last 16, while the Reds went all the way to the final after knocking City out in the quarter-finals.

With five Premier League sides finishing in the top eight of this season’s league phase, and therefore avoiding the prospect of facing one another in the last-16, there is the chance of a record number of English teams making the quarter-finals.

Having numerous English clubs in latter stages of the Champions League is nothing new with four sides progressing to the quarters in both 2007-08 and 2008-09, as well as 2018-19 – leading to an all-English final in 07-08 and 2018-19.

No other country have ever had four teams in the quarter-finals – this year England could have as many as six.

But the demands of playing in the Premier League alongside the Champions League takes its toll, which is why many managers were relieved to avoid the two extra play-off games.

“I still think it will be very difficult for one of them to go on and win it, just because of how difficult the Premier League is every week – whether you are fighting for the title or for a place in the top four,” Warnock added.

The three other countries who had teams join English sides in progressing to the knockouts were Germany (Bayern Munich), Spain (Barcelona) and Portugal (Sporting CP).

That has left some surprises having to go through via the play-offs, with Paris St-Germain failing to get the win they needed against Newcastle to secure a top-eight spot.

Real Madrid, meanwhile, were on the wrong end of a thrilling and dramatic match with Benfica.

Real were reduced to nine men while a last-second goal by goalkeeper Anatoliy Trubin secured a memorable 4-2 win for Jose Mourinho’s side that earned them a play-off spot.

Other big sides who are facing the lottery of the play-offs include Italian sides Juventus and Inter Milan, along with Germany’s Borussia Dortmund and Spain’s Atletico Madrid – who were stunned by Bodo/Glimt on Wednesday.

The Norwegians have been the surprise package of the Champions League and their win against Atletico came just eight days after they beat Manchester City.

Watch highlights of every Champions League game from 22:00 on Wednesday on BBC iPlayer and the BBC Sport website and app.