Aidy Boothroyd's England are on the verge of a group stage exit from the Under-21 European Championships following a 2-0 defeat to Portugal.
Dany Mota struck in the 64th-minute to give Portugal a deserved lead and Barcelona's Francisco Trincao doubled the advantage from the spot 10 minutes later as Rui Jorge's side made it two from two in Group D.
Boothroyd made four changes from the side that lost 1-0 to Switzerland on Thursday but England produced another below par performance to leave them on the brink of another embarrassing premature exit from the competition.
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The first-half was a drab affair with chances at a premium. Portugal went closest, with Ben Godfrey clearing Dany Mota's header off the line while Aaron Ramsdale was forced into saves from Thierry Correia and Vitinha.
Portugal took control after the restart and when Oliver Skipp lost possession, England were caught short defensively as Pedro Goncalves slipped through Mota who stroked it past Ramsdale with a first-time finish.
Things went from bad to worse for England as just moments after Boothroyd made a double substitution, Marc Guehi stood on the ankle of Goncalo Ramos - who was only on the pitch a matter of seconds - and the referee pointed to the spot, with Trincao slotting the penalty past Ramsdale.
There was no way back for England, who failed to produce a single shot on target, and they now need to triumph over Croatia on Wednesday and hope Portugal can beat Switzerland to have any chance of progressing to the group stages.
Even that may not be enough as it would then come down to a three-way, head-to-head between England, Croatia and Switzerland for the runner-up spot.
TALKING POINT - England on the brink of another early exit
Two years after England crashed out of the group stages after suffering back-to-back defeats, the young Lions somehow find themselves in an identical predicament.
Back in 2019, Aidy Boothroyd stressed his side were 'on the right track'. If anything, the Under-21 are only going backwards judging by their performances in this competition. They have registered only one shot on target across two games. Simply unacceptable considering the array of attacking players Boothroyd has to choose from. It is evidently clear that the manager is failing to get the best out of what - on paper at least - is a talented group.
It's not quite over, but England need a minor miracle to qualify now. With Boothroyd's contract due to expire in the summer, it seems his tenure will end on a desperately disappointing note.
MAN OF THE MATCH - Pedro Goncalves (Portugal)
Manchester United have been linked with the Sporting Lisbon forward and on this performance, it is no surprise. He has been setting Primeira Liga alight this season, chalking up over 15 goals and assists, and he underlined his quality on the international stage with a supreme display. His beautifully weighted pass to set up Portugal's opener encapsulated a wonderful night for the 22-year-old.
Portugal: Costa 6, Correia 7, Queiros 6, Leite 7, Dalot 7, Florentino 7, Vitinha 8, Fernandes 7, Vieira 7, Mota 8, Goncalves 9.. subs: Braganca 6, Conceicao 7, Ramos N/A, Soares N/A, Trincao 7.
England: Ramsdale 6, S Sessegnon 5, Guehi 5, Tanganga 5, Godfrey 7, Skipp 5, Davies 5, Smith Rowe 5, Madueke 6, R Sessegnon 5, Nketiah 5.. subs: Gallagher 5, Jones 5, Eze 6, McNeil 5, Brewster N/A.
64' - GOAL! Portugal 1-0 England (Dany Mota): Portugal deservedly lead and now England are in a world of trouble! England are simply outnumbered after Skipp loses possession. Goncalves drives forward and slips through Mota with a beautifully weighted pass and he makes no mistake, stroking it past Ramsdale with a first-time finish.
73' - Penalty to Portugal! Guehi stands on the ankle of substitute Ramos - only on the pitch a matter of seconds - and the referee points to the spot!
74' - GOAL! Portugal 2-0 England (Francisco Trincao, pen): Trincao gives Ramsdale no chance with a perfect penalty, sending the England goalkeeper the wrong way. It's a long way back for England now.
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