England's hopes of a first trophy in 53 years went up in smoke in calamitous fashion as dreadful defending allowed Holland to seal a 3-1 extra-time victory and progress to the inaugural Nations League final.
Disrupted preparation was followed by embarrassing fan disorder before Thursday's semi-final in Guimaraes, where the Three Lions had looked set to seal their place in Sunday's finale against Portugal and a shot at their first piece of major silverware since the 1966 World Cup.
Marcus Rashford's first-half penalty was cancelled out by Matthijs De Ligt, but substitute Jesse Lingard sent England fans wild by coolly slotting home in the 83rd minute - a goal that only fleetingly had the country in dreamland.
Video assistant referee Francois Letexier ruled the goal out for the narrowest of offsides and Holland punished Gareth Southgate's men as they suffered an extra-time semi-final loss for the second successive summer.
Croatia brought their World Cup journey to a crashing end last year and this time inexplicable dawdling by John Stones put Holland on course for victory.
The defender lost De Ligt for Holland's leveller and then watched as Kyle Walker turned into his own net under pressure from Quincy Promes having inexplicably given away the ball.
The heartbreak did not stop there as Ross Barkley became the latest to overplay at the back, with his poor touch lapped up by Memphis Depay who squared for Promes to score.
It was a heartbreaking fourth successive semi-final loss that underlines the work still required for Southgate, who now faces the unenviable task of rousing the troops for a third-place play-off against Switzerland on Sunday.