The craziest finish in UEFA Champions League history?! Goalkeeper scores at the death against Real Madrid to send Benfica into play-offs

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Jose Mourinho oversaw one of the most incredible moments in UEFA Champions League history on Wednesday as his goalkeeper scored a dramatic, last-gasp header against Real Madrid to keep themselves alive in the competition. Mourinho's side were heading out, while Madrid were chasing a top-eight spot, before chaos ensued in Portugal. Watch the Champions League on TNT Sports and discovery+.

Watch: Benfica GK scores DRAMATIC header against Real to send Mourinho wild

Video credit: TNT Sports

In one of the most dramatic finishes to a UEFA Champions League game ever, Benfica goalkeeper Anatoliy Trubin scored a 98th-minute header against Real Madrid to keep Jose Mourinho's side alive.

The late goal meant Los Blancos failed to finish inside the top eight, while the Lisbon giants clinched a play-off spot by knocking Marseille out on goal difference.

At 3-2 down in the late stages, nine-man Madrid - who had Raul Asencio and Rodrygo both sent off in normal time - were pushing for an equaliser which would have seen them earn automatic qualification to the last 16.

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But Benfica, outside the top 24 by a single goal, surged into Madrid’s half as Fredrik Aursnes drew a foul from Jude Bellingham, which gave the home side the chance to put the ball in the box for what would surely be their final chance of survival.

With nothing to lose as the match ticked over into the 98th minute, goalkeeper Trubin charged up the pitch to join his team-mates in the Madrid box.

"Come on, get this in the mixer," Joe Cole said on TNT Sports' Goals Show Extra as the pundits eagerly watched on.

And what happened next sent them into chaos. Trubin towered over everyone before guiding a brilliant header, which most strikers would have been proud of, beyond Thibaut Courtois to score in the most dramatic of circumstances.

"The keeper! Oh my god! Unbelievable! Unbelievable!" presenter Matt Smith cried. "I think the roof just came off Estadio da Luz! That is incredible."

Trubin became the fifth different goalkeeper to score a goal in the Champions League, joining Jorg Butt, Sinan Bolat, Vincent Enyeama and Ivan Provedel in the elite group.

Ally McCoist later added: "We were all watching it, and we anticipated that something was going to happen.

"You just had a feeling. With the Mourinho factor, the whole thing is remarkable."

And the twists and turns do not stop coming, as Benfica will now face either Internazionale or, incredibly, Real Madrid in the play-offs - two of Mourinho's former clubs.

Should they face Madrid, Wednesday's famous win will do Mourinho the world of good, as he has had a tough time navigating his way past his former side.

The victory was Mourinho's first against Madrid in his sixth attempt across all competitions.

Before that, the Spanish giants were the side Mourinho had managed against most in his career without recording a victory.

The scoreline meant that Benfica pipped Marseille to the 24th spot - the final play-off place to compete for a spot in the last 16.

Meanwhile, Madrid finished ninth overall, one point behind Manchester City, who took the final guaranteed spot in the last 16.

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