Emiliano Buendia missed a second-half penalty as Aston Villa suffered a surprise Europa League defeat in Deventer to a spirited Go Ahead Eagles side.
Evann Guessand’s early fast finish appeared to be the harbinger of Unai Emery’s team keeping their perfect record in the competition.
However, the hosts equalized with Mathis Suray’s deflected shot just before the break and took the lead when Mats Deijl sneaked in just after the hour mark to lift the ball over Villa goalkeeper Emiliano Martinez.
And when Buendia converted his spot kick in the dying moments after home defender Dean James was punished for handball, the packed De Adelaarshorst stadium exploded in celebration.
It clinched a remarkable triumph for the Eredivisie club, which qualified for the competition by winning the Dutch Cup the previous season, their first major title in 92 years.
However, it will be a humiliating setback for Villa and Emery, who initially thought to have been vindicated for making wholesale changes following their Premier League victory over Tottenham last Sunday.
The result puts Villa seventh in the rankings, while the Dutch club moves up to tenth, also on six points, ahead of Thursday evening’s later kick-offs.
For the whole of the first quarter, there appeared to be a substantial disparity in skill between the teams, with home goalkeeper Jari de Busser at fault as Guessand assisted the visitors in taking control.
The Ivory Coast forward should have extended Villa’s lead after breaking through on goal just before halftime, but he enabled De Busser to spread himself and save from close range.
When the Belgian goalkeeper produced another excellent save to deny Jadon Sancho’s low effort from finding the bottom corner, it appeared only a matter of time before Villa’s dominance was rewarded with a second goal.
Instead, the visitors’ high defensive line was exposed as Suray’s shot looped off Tyrone Mings and into the upper left corner.
A second error cost them the game when a dozing back four allowed Deijl to sprint onto a long pass forward.
Emery will be concerned about how Villa lost this match from such a strong position and on the heels of a five-game winning streak in all competitions.
For much of the first half, the Spaniard watched his team miss opportunities to put the game away against opponents who are ranked 12th in the Dutch top flight.
Buendia, Ollie Watkins, and Mings all should have done better with golden opportunities, and Villa’s ineptitude eventually gave the hosts enough motivation to claw their way back into the game.
“Even dominating chances, we conceded mistakes, some chances. We must accept it. We have broken the good form we have, and I hope we recover quickly,” said Emery.
“They had motivation, and their goal helped them to feel stronger. The second goal we conceded we have to try to avoid. In the second half we dominated, but we conceded a few chances, and they were clinical. They deserved it.”
The Go Ahead Eagles had barely spent any time in Villa territory, and the visitors had 12 shots to Villa’s three until Suray leveled.
Surprisingly for Emery, once his squad lost control, they were never able to restore it.
John McGinn, Morgan Rogers, and Donyell Malen were all summoned from the bench, although their contributions were limited to a cross from the England striker that hit the crossbar.
And Buendia’s miss, Villa’s fourth in five penalties in Europe, condemned them to their first defeat against a Dutch team.
