England opened their Under-21 European Championship account with a disappointing defeat to Portugal at Mestsky Fotbalovy Stadion.
Gareth Southgate's much fancied outfit, who were rocked just hours before kick-off by the news that Saido Berahino will miss the entire tournament due to a knee injury sustained in training, showed flashes of promise throughout the 90 minutes but were ultimately left frustrated after ceding the midfield battle against their undeniably talented opponents.
The early stages of the match were played at a frenetic pace, with both sides looking to retain possession and utilise the flanks. Tom Carroll showed early promise when threading a cute ball through to Harry Kane, but the Tottenham Hotspur striker had strayed marginally offside.
Nathan Redmond and Jesse Lingard looked dangerous from the outset and the former had England's first sight of goal when he combined well with Carl Jenkinson down the right-hand side before stinging Jose Sa's palms with a fierce drive that the Portuguese stopper could only push wide.
Jack Butland was then forced into a smart reaction save after just seven minutes when a dangerous cross took a heavy deflection off Liam Moore and the Leicester City defender was then forced to backtrack as Bernardo Silva sauntered forward before releasing a tame shot that was comfortably saved.
Joao Mario should have done far better with a wild effort that soared high over the crossbar after good work from Raphael Guerreiro, while Ben Gibson could not direct a header on target after Kane had won a corner.
Lingard, a late inclusion in the starting lineup in place of the unfortunate Berahino, was evidently keen to make the most of the opportunity and his well-struck shot in the 19th minute flew marginally over with Jose Sa scrambling.
Moore was then called upon once more to block from Joao Mario after the midfielder had recovered from an unfortunate slip in the penalty area.
Portugal began to take control of the midfield exchanges midway through the first half, but remained rightfully weary of Kane's talents as he first forced a diving save from Jose Sa down to the goalkeeper's left before firing into the side netting from distance.
Liverpool's Tiago Llori spurned a good chance when he nodded Silva's free-kick just wide of Butland's left-hand post and Moore was slightly lucky not to be punished when he was outmuscled by Ivan Cavaleiro during a misguided attempt to shield the ball out of play.
Having registered England's first opportunity in the first half, Nathan Redmond also started quickly after the break and another powerful drive was unconvincingly dealt with by Sa.
James Ward-Prowse came agonisingly close to the opening goal when he curled an excellent right-footed free-kick inches wide.
Raphael Guerreiro failed to test Butland with a venomous strike but Portugal edged ahead just moments later as England were guilty of some horrendously slack defending as Joao Mario made no mistake from close range after Silva had hit the post.
Such an advantage should have been doubled shortly after the hour mark, but Ricardo's header lacked composure after he was picked out by an impressive cross from the lively Joao Maria.
You could certainly forgive Kane if he was feeling a touch frustrated over a lack of quality service and his 69th-minute effort was well blocked by William Carvalho. A lacklustre header from the resulting corner did not trouble Jose Sa, nor did a wasteful free-kick from Luke Garbutt.
By now, England were toiling badly in their attempts to break the monopoly of Portugal's confident midfield marshalled by the excellent Carvalho. Substitute Alex Pritchard made a quick impact after replacing Carroll and found club teammate Kane but his quick, left-footed shot was well saved.
With the game slipping away, Danny Ings, on for Lingard, fired wide with a fine strike before Carvalho was afforded time to turn on the edge of the penalty area but his low effort was deflected behind.
Southgate's side poured forward in desperation during three nervy minutes of stoppage time. They could not find that all important equaliser, however, with Pritchard twice looking to force the initiative to no avail and Nathaniel Chalobah denied a shooting opportunity at the critical moment.
The loss was England's fifth in succession at the Euros following the debacle than ensued under Stuart Pearce in Israel two years and only their second since former Middlesbrough boss Southgate took charge in August 2013.
Such a defeat leaves the young Lions third in Group B following Italy's 2-1 defeat to Sweden earlier.
England face Sweden next at the Andruv Stadion in Olomouc on 21 June.