European Under-21 Championship favourites France were knocked out as the Netherlands, Portugal, Spain and Germany claimed semi-final spots. France, boasting a squad littered with senior internationals that included some of the hottest prospects in European football, lost 2-1 to the Netherlands thanks to Myron Boadu's last-gasp goal.
Dayot Upamecano, who will play for Bayern Munich in 2021-22 following his move from RB Leipzig, opened the scoring for Les Bleus, but Boadu equalised early in the second half.
And despite finishing with 14 attempts – six of them on target – France suffered a disappointing exit when Boadu finished on the counter in the 93rd minute, Houssem Aouar having headed a glaring chance over at the other end.
That game was the only one on Monday not to go to extra time.
Two goals from substitute Javier Puado put holders Spain through at the expense of Croatia, who had equalised through Luka Ivanusec's 94th-minute penalty.
Portugal and Italy then played out an eight-goal thriller.
Dany Mota's brilliant double – which included an exceptional overhead kick to break the deadlock – put Portugal into a commanding lead, only for Italy to hit back through Tommaso Pobega.
Goncalo Ramos' goal seemed to have settled the contest, yet Gianluca Scamacca and Patrick Cutrone made it 3-3 at the end of 90 minutes.
However, Matteo Lovato's second booking dented Italy's chances in the first extra period, setting the stage for Jota and Francisco Conceicao to seal a 5-3 win for Portugal, who will face Spain in the last four.
The other tie was settled by penalties, Germany and Denmark having finished level at 2-2 after 120 minutes.
It required sudden death in the spot-kick scenario too, but Victor Kristiansen saw his effort saved before Paul Jaeckel made no mistake to seal a 6-5 shootout win, with the Netherlands coming next for the 2019 finalists.