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. "I am not used to scoring, so for me it was something completely new. I am 24 years old and for me it's the first time."

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. "Looking at the results, it's pretty incredible. They started so poorly and after Leverkusen at home we thought that's it, they're done, but there was still a bit of life in them and we saw that today in that miracle."

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. But beating Trubin's magical moment might be a stretch, even for Mourinho's scriptwriters.

Watch highlights of Champions League games on BBC iPlayer and the BBC Sport website and app.