For Jose Mourinho, at this stage of his long and drama-filled career, the first time won’t be easy to come by.
But on Wednesday night in Lisbon, Anatoly Trubin provided just such a moment.
For Benfica, simply beating 15-time Champions League champions Real Madrid wasn’t enough.
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They led 3-2 in stoppage time but needed another goal or their Champions League journey would be over.
A free kick gave them their last chance, with goalkeeper Trubin pushed forward.
Moments later, with chaos at the Stadium of Light and Benfica players running for cover, Trubin ended his wild charge with a sliding knee and scored the decisive goal with a bullet header.
Mourinho said: “It was a wonderful goal, a historic goal, a goal that almost brought the entire stadium to its knees and I think we deserved it.”
“For Benfica to beat Real Madrid is an incredible prestige.”
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Considering the way the league format is played with 18 games played simultaneously on the final matchday, it’s no wonder Trubin doesn’t fully realize what his team needs.
They were out on goal difference at the end of the eight-game league stage until his brilliant intervention. Marseille were the unlucky side to drop out of the play-off places after Benfica snatched their place away from them after drama in Lisbon.
Minutes before the goal, Trubin fell to his knees after receiving a cross, seemingly trying to waste a few seconds to wrap up the victory, unaware that Benfica was still out as it was.
“Before, I didn’t understand what we needed,” Trubin said. “I saw everyone started pointing at me and I walked away and then I saw [I can go forward]. We also need a goal.
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“I don’t know, I don’t know what to say. It’s a crazy moment.
“I’m not used to scoring goals, so it’s something completely new for me. I’m 24 years old and it’s the first time for me.”
Mourinho trusts Trubin’s threat with ‘huge’ win
Anatoly Trubin becomes fifth goalkeeper to score in Champions League [Getty Images]
Mourinho’s adaptation process has not been easy since returning to Benfica in September.
There was already a degree of skepticism when the ‘Special One’ was appointed, some 25 years after his first (very brief) spell at the club, and there was a sense that the 63-year-old was well beyond his prime.
Four and a half months on, Benfica are unbeaten in the league but in third place, 10 points behind leaders Porto, who have 55 points out of a possible 57. Mourinho’s chances of adding a ninth league title to his collection look extremely slim.
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Meanwhile, in Europe, they lost their first four games of the league stage and even after losing to Ajax and Napoli in the penultimate round, it looked like it wasn’t enough.
His team also bowed out of the domestic cup after losing in the quarter-finals to Porto, the team Mourinho made famous more than 20 years ago.
That game on January 14 proved to be a trial run for Trubin’s Champions League heroics.
“We know he can do it,” Mourinho told UEFA. “In the match at the Dragon Stadium, Trubin also scored a header at the last minute, but it was blocked by a Porto player.”
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The Ukrainians would not be denied this time, with immaculate movement and a superb header pulling Benfica back from the brink and keeping their European hopes alive.
European football expert Julian Lawrence told BBC Match of the Day: “It’s huge for Mourinho because things haven’t been going well for him since taking over from Bruno Lage in September.”
“Winning this way tonight, the story is there. Against his former club Real Madrid, against his former club [Madrid coach Alvaro] Arbeloa, his mentor and whom he considered his own son, sat on the other bench.
“Looking at the results, it’s unbelievable. They started really badly and after the home game against Bayer Leverkusen we thought that was it, they were done, but they still had a little bit of energy and we saw that today in that miracle.”
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Madrid rematch or return to Inter Milan to wait
For Mourinho, beating Real Madrid is something worth cherishing.
“The win against Real Madrid is very important, it means a lot. At that moment we have to give it our all,” Mourinho said.
The former Chelsea boss spent three seasons at the Santiago Bernabeu between 2010 and 2013, playing alongside Pep Guardiola’s mighty Barcelona and winning the La Liga title in 2011-12.
Guardiola is wary of how the latest chapter in Mourinho’s story unfolds, and he and his Manchester City players are keen for Benfica to continue their winning streak to ensure the Premier League side finish in the top eight.
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“We didn’t know that Benfica needed to score to advance, so when the goalkeeper came on we asked, ‘Why did you go?’, because Real Madrid could have equalized and we were out,” Guardiola said after City’s win over Galatasaray.
“But it was a good strategy for Jose to score the fourth goal, right?”
Another battle with Guardiola may have to wait, but Mourinho has just earned his first win against Real Madrid and is likely to get a second in February.
With Arbeloa’s team ranked 9th in the league and Benfica 24th, they have a 50% chance of meeting in the play-offs.
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The other side Benfica could face? Inter Milan, Mourinho led Inter Milan to win the Champions League in 2010, achieving the famous Triple Crown.
“I can’t say I prefer one over the other because going to Madrid I liked it a lot but I didn’t go there; going to Milan I liked it a lot but I didn’t go there either,” Mourinho said.
Whoever Benfica draws, few would rule out Mourinho plotting something special at the Bernabeu or San Siro.
But even for Mourinho’s writers, beating Trubin’s magic moment might have been a bit difficult.
Watch highlights from every Champions League match on BBC iPlayer and the BBC Sport website and app from 22:00 on Wednesday.
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BBC One will also show daily Champions League matches on Wednesdays from 22:40 to 00:00.