Newcastle United endured late agony in Lisbon against Benfica after finishing the game with 10 men following a red card for Joelinton.
The Brazilian was dismissed for two yellow cards in an incident that sparked an angry clash with the Toon bench and officials in the closing stages.
To rub salt into open wounds a last gasp winner from Henrique Araujo - with penalties looming - secured the Eusebio Cup for the home side.
READ MORE: Recap the defeat to Benfica as it happened
When the dust settles the clash will be deemed a useful work out for Eddie Howe's side after they took the game to Benfica with Miguel Almiron proving a first half two-goal hero with a brace.
The game had kicked off in balmy conditions in Portugal with Howe handing Elliot Anderson a start to the left of a three-man midfield.
Benfica had the first opening of the night when Portugal star Joao Mario floated a cross in for Gilberto but he tamely headed at Nick Pope.
United's first real chance came with five minutes on the clock when Miguel Almiron skipped into the penalty area and tried his luck but struck the ball wide with the outside of his left foot.
Callum Wilson was screaming for it at the back post but the ball rolled harmlessly wide of the target.
Yet Almiron would enjoy more fortune in front of goal later in the game in one of his best performances in a black and white shirt.
Benfica were posing questions of the Newcastle defence through Mario in the opening exchanges and it was his perfectly floated corner that led to the first goal on 14 minutes.
The ball was curved in at pace for Goncalo Ramos who rose above Jamaal Lascelles and headed home despite Pope's attempts to punch the ball clear.
Newcastle were level eight minutes later though after brilliant work from Almiron.
The Paraguay captain swept a pass out to Kieran Trippier on the right before his cross into the penalty area found Almiron who swept home the equaliser in Lisbon.
Moments later Rafa Silva got the better of Trippier but his effort was just inches wide of the top right hand corner.
A Bruno booking for a foul on Rafa in the first half left the Brazil star walking the tightrope, especially with Benfica's play acting resulting in a host of debatable fouls.
On 28 minutes Allan Saint-Maximin's probing run on the left-hand side found Wilson in the box but Greece international Odysseas Vlachodimos smothered the ball in the box.
Benfica earned a free-kick when Bruno upended Enzo 20-yards from goal. And it proved to be a costly moment despite Newcastle protests for another soft foul.
Mario left the ball to Grimaldo and the Benfica star swept home into the top right-hand corner with Pope unable to get a finger to it.
With 33 minutes gone Pope made a double block to deny Mario then Ramos after the latter had tried an audacious rabona at the back post.
However, Newcastle were level just before half-time after more good work involving Trippier and Almiron.
Trippier slipped it to Almiron in the box and the South American opened up his body before curving it past the keeper to make it 2-2.
Despite some hairy moments with Benfica looking dangerous pushing forward, Newcastle were good value to go in level at the break.
Howe opted to make 11 changes for the second half with Karl Darlow replacing Pop and a back four of Emil Krafth, Fabian Schar, Dan Burn and Matty Bondswell.
Jonjo Shelvey, Joe Willock and Joelinton made up the midfield while a front three of Matt Ritchie, Chris Wood and Jacob Murphy formed a three pronged attack.
The multiple changes resulted in the game settling down compared to what can only be described as a ferocious first half.
A tame Wood shot was struck straight at the goalkeeper but the game drifted past the hour mark with the teams locked at 2-2.
Shelvey's long pass found Murphy with 20 minutes left but he struck the ball at the keeper and wasted the opportunity.
Seconds later Shelvey's cross found Wood but he headed straight at Vlachodimos who gathered easily.
But with 15 minutes left Shelvey was hit with some injury woe as he was fouled and fell awkwardly with Howe advised to replace him.
It was Matty Longstaff who came on for the final throes of the night with the midfielder facing an uncertain future on Tyneside but getting a chance at a prestigious venue like Benfica.
Tempers flared when Joelinton was sent off for a second yellow card after a foul on Florentino with eight minutes left.
And there was agony when Benfica took the lead in the 89th minute when Ramos beat Burn in the box before cutting the ball back for Henrique Araujo to apply the finish and roll it past Darlow.
A third equaliser was beyond Newcastle and they watched on as Benfica lifted the Eusebio Cup for the fourth time in their history after a tough defeat.
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