Jose Mourinho's Eagles were out of Europe entirely, and Real Madrid were in the top eight that qualify for the UCL stages automatically in the final minute of the match when the two teams met in what was game number eight of the league stage.
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Trubin to the rescue
Step forward Benfica keeper Anatoliy Trubin to score what must rank as one of the most important goals of all time in the competition.
Not only did it cement the Portuguese side's win over the serial winners of the cup with the big ears, but it condemned Los Blancos to the play-offs, and took Benfica into them by the skin of their teeth.
No wonder former manager Mourinho enthusiastically joined in the celebrations. It truly was a footballing moment for the ages.
Although the Spanish giants will remain the heaviest of favourites going into the two-legged tie, and have won eight of their last 10 UCL games against Portuguese sides (D1, L1), they have lost three of their four meetings with Benfica (W1).
Real's poor recent UCL record
It's also worth noting that in their last 11 Champions League matches, Real have been defeated six times, as many losses as in their previous 39 games in the competition.
The visitors have scored in four straight Champions League games in 2025/26, though, and no team has been able to stop them from scoring since their loss to Liverpool during the league stage.
Furthermore, Benfica have won only two of their last eight UCL matches against Spanish opposition and have won only twice at home in the competition this season.
However, one other factor in the hosts' favour is that they play bottom-of-the-table AWS at the weekend in the league, a fixture in which they can rotate heavily.
Real have a reasonably tricky assignment away at Osasuna. They've only won three of the last six at El Sadar in LaLiga, and in order to keep Barcelona at arm's length, nothing less than a hard-fought victory will be acceptable.
Mbappe set to make more history
What makes this match even more intriguing is that both teams have remained unbeaten in games since their last meeting, with Real managing to do so despite not being able to call upon the services of Kylian Mbappe, Jude Bellingham and Rodrygo, the latter two of whom are almost certainly out of this game.
Mbappe's 13 goals in seven European appearances are the highest goals-per-game ratio of any player who has played more than five games in a single Champions League/European Cup campaign, so Alvaro Arbeloa will be counting on the services of the French marksman if he recovers from his injury in time.
A late fitness test will determine Mbappe's availability, be that as a starter, a substitute or kept in reserve for the second leg in a week at the Santiago Bernabeu.
Benfica have a great marksman of their own in Vangelis Pavlidis. The 27-year-old continues to impress at the highest level and already has nine goals in this season's competition.
One more in either leg of this tie would ensure he becomes just the second Benfica player, after Oscar Cardozo, to get to double figures in a single UCL campaign.
Whatever happens, the Santiago Bernabeu awaits...
Mourinho won't really need to motivate Pavlidis or the rest of his players in order to be at their very best over the two legs, given the standard of the opposition, though Benfica do have the opportunity to make it three successive UCL home wins in a season for the first time since the 1994/95 season.
Not to mention that it would be very 'special' for the Special One to get one over on his old employers, and his current playing staff will almost certainly have that in the back of their minds too.
Whatever the result on Tuesday night, to use an old footballing phrase, 'it's only half-time in the tie.'
Even if Benfica were to spring another surprise on the LaLiga table-toppers in Portugal, it will take a huge collective performance in the return leg next Wednesday in Madrid for the Eagles to progress into the knockout stages.
The Santiago Bernabeu remains the scene for some of Los Blancos' greatest European triumphs and, whilst their form this season could be classed as patchy at times, Real will be difficult to overcome at home.
Something that Mourinho will know only too well.
