Joao Mario's 57th minute goal for Portugal U21 saw them beat an ambitious England U21 side 1-0, who deserved a loss after a sleepy second half in the Czech Republic.
England started the first half in brilliant style, Nathan Redmond standing out from the high-profile names in the two sides. Yet they died down after 30 minutes.
Although they looked good in the second half, Joao Mario pounced on the rebound of Bernardo Silva's post-striking shot to give Portugal the lead.
Alex Pritchard was the main instigator of a come-back in the latter stages but couldn't grab the point despite a huge amount of chances in added time.
England start well
Nathan Redmond was the first of England's high-profile players to make an impact as the Norwich forward delivered a beautiful ball across the penalty area, just evading Harry Kane.
That pattern of England settling well continued in the early stages as possession was kept well by the Young Lions. The patient play into attack ensured that Portugal's pace in attack couldn't break away, as Gareth Southgate mentioned was the major threat.
Kane's movement, improved throughout his season in the Premier League, got an early show as he slipped through the Portugueuse back line and onto Tom Carroll's pass, only to be called offside by the smallest of margins.
Portugal's pace showed in the fifth minute as within seconds of intercepting the ball they pressurised the England area. Nothing came of it as England cleared for a throw-in, but the demonstration of danger came early on.
A great, reaction save from Jack Butland was his first piece of action in the Czech Republic as the captain saved vitally from his own player. Esgaio's curling cross was tipped into Butland's direction by Liam Moore and he produced a brilliant out-stretched hand to stop Portugal going up early on.
James Ward-Prowse then took advantage of the space around him by unleashing a rising shot, which swerved up and over the cross bar.
The quick-paced start from both sides died down ever so slightly with ten minutes but Nathan Redmond ensured that changed as he powerfuly struck a laced-shot at Jose Sa, earning a corner which was wasted.
Bernardo Silva made a tricky run before striking a daisy-cutter from the edge of the box for Butland to catch before some wonderful build-up play, involving great footwork saw Mario lined up for a chance. Yet the Portugal man lent back too far and his shot sailed over the crossbar.
Carl Jenkinson made a good run with the ball down the right-flank, bursting out from his right-back position, and earned a corner. Yet again, it wasn't used wisely, headed away with ease by the Portugueuse defence.
Redmond creating everything for England
Redmond's yellow boots provided a blur of danger as he powered down the right wing before driving inside towards Jesse Lingard who shot from 25-yards with a curling, powerful strike, just over Jose Sa's crossbar.
Once more, Redmond provided something for England, starting off a lovely passing move on the left-flank this time, before playing a cross-field ball to Lingard. His looping cross to Kane missed the Spurs striker by inches but he regained the ball quickly, combining with Redmond well consistently.
Sergio Oliviera had an ambitious effort from 30 yards out of Butland's goal but it whistled over the bar by metres, not inches.
Ivan Cavaleiro twisted in and out without moving forward before having his shot blocked as Portugal looked to threaten the English defence after a quiet few minutes for their attack.
As the half hour mark approached, both sides calmed down after a long period of constant attacking full of pace.
Kane had a fantastic effort saved by Jose Sa. As shown in his breakthrough season last year, he found himself a small area of space, strode into it and unleashed a curling effort onto Sa's far post. The Portugal goalkeeper tipped it wide but the danger of Kane when he finds the space showed after thirty minutes or so.
With the confidence of that shot in his mind, Kane found space again, exploiting the gaps in Portugal's defence as his shot whistled past the left post.
Riciardo delivered a wonderful, head-skimming free-kick which Tiago Ilori headed wide as he looked to be shoved forwards slightly.
The fifteen minutes before half time only contained the three chances compared to the previous thirty minutes bundle of shots and attacks. The game tired in the last few minutes before the break, especially, as Redmond, Lingard, Cavaleiro and Bernardo Silva stopped making quick breakaways.
The second period began as the first ended, with possession the main aim for both sides as caginess continued to flourish over attacks.
Nathaniel Chalobah cut out a ball, strode forward and used the outside of his boot to send it forwards quickly, the counter attack used again. England played it around on the edge of the box, with Portugal playing very narrowly before Redmond struck with unexpectedly brilliant power from his weaker foot, Jose Sa saved.
Ben Gibson picked up the first booking of the match before the free-kick from Portugal started a quick England attack, much like in the opening half an hour.
Gareth Southgate had clearly told his team to use their pace again to counter, as James Ward-Prowse's free kick smashed against the advertising board, curling wide of the left post. Bernardo Silva picked up the second booking of the match for that free-kick, having fouled Lingard.
Ward-Prose was replaced by Derby County's Will Hughes after his free-kick chance for an assumed small knock, even if though he looked okay when running off the pitch.
Joao Mario gives Portugal 57th minute lead
Despite England's second half domination of possession and occasional chances, Sporting Lisbon's Joao Mario gave Portugal the lead. Shots rained in on Jack Butland's goal, where chances had been at a minimum, as Bernardo Silva hit the post, before eventually the net lay empty for Mario to strike firmly into the back of it.
A change of approach was necessary but Southgate left things to be for a few minutes. With new found confidence, Portugal's influence increased, with Bernardo Silva using his great footwork to seamlessly transfer defence into attack.
Frustration crept into England's game, as Portugal dominated the midfield, allowing players like Silva and Cavaleiro to use their flair on the ball in attack. Carl Jenkinson picked up a booking for a poor challenge on Cavaleiro, who limped away for the free-kick that Butland caught easily.
Ricardo had a good opportunity to double things up for Portugal as the cross landed on his head perfectly. Yet his jump was too low and the ball rose as soon as it hit off his head, going wide and over.
Carvalho gave away a free-kick, always dangerous with Garbutt on the pitch for England, with a foul on Jesse Lingard. Yet, from 27 metres, Garbutt chipped the ball over the bar, a real waste of a free-kick in a good position for a cross.
Service for Harry Kane, the big name in the side, had been poor so he dropped back to pick up the ball. He strode into space out of the box before earning a corner with a laced shot. Jose Sa claimed the ball from the set piece, as England wasted another opportunity.
Both Portugal and England made substitutions at 73 minutes, with the former looking to seal things up and the latter looking for fresh legs and creativity.
England not creative
Jesse Lingard came off for Danny Ings as Gareth Southgate looked for fresh creativity and Iuri Medeiros came on for Ivan Cavaleiro. Both Lingard and Cavaleiro had wonderful first halves before failing to replicate it in the second period.
The goal from Portugal still showed on the England faces, all eleven players looking knocked out by Mario's opener. Chances were missing, Redmond's quick counter attacks disappeared and nothing had changed from the minute after the goal.
Carlos Mane came on for Ricardo Pereira with just over ten minutes to go.
Kane had been given no chances since the goal but after Pritchard replaced Tom Carroll, he struck well on the turn, but too close to Jose Sa to get the equaliser.
That chance, the first in too long, made England realise they had been asleep. Tackles came in quicker, they were crisper, just like the passes and finally Kane's teammates got him involved in the game.
Danny Ings had his first shot, a first time one, from 20 yards but the keeper saved easily. Ruben Neves, another addition to the high-profile stack of players building up on the pitch, came on for Joao Mario.
Bernardo Silva hadn't produced magic for a few minutes so drove out of a deep position, creating luck and time for himself, not relying on others.
William Carvalho, present all game, had a shot on the turn from 25-yards, but it dribbled quietly past the right=post of Jack Butland's goal.
Kane played in Pritchard, sitting on the corner of the box, who produced a wonderful cross full of swerve away from the goalkeeper to Danny Ings but Jose Sa picked up the ball brilliantly with an excellent dive to Ings' feet.
Pritchard scuffed a chance into the ground, the ball falling nice to him, as it bounced wide of the goal.
England retained hope as three minutes were added on but chances were limited and when they did come, it was a long range shot like from Pritchard earlier.
Chalobah earned a corner with a driving shot that Carlos Mane deflected out but again it was a waste of a set-piece and Portugal broke with speed, looking to seal the three points.
Pritchard continued to be the centre of things, crossing once to Ings and Kane, shooting for a corner before delivering the corner with a wonderful cross to Jenkinson, who hit wide.
The referee's whistle indicated the end of a desperate scurry to regain a point at the very least having looked shell-shocked as soon as Portugal took the lead through Joao Mario.
