England failed to confirm their place at Euro 2020 after suffering their first qualifying loss in 10 years as the Czech Republic came from behind to win 2-1 in Prague on Friday.
Harry Kane's early penalty put Gareth Southgate's men on course to continue what had been serene progress through Group A, but Jakub Brabec quickly levelled for the impressive Czechs.
Substitute Zdenek Ondrasek then struck the winner five minutes from time to inflict England's first qualifying defeat in 44 games since a 1-0 loss to Ukraine in 2009.
England still top the group thanks to their better head-to-head record with the Czechs on 12 points, but have work to do in their final three qualifiers, starting with a visit to Bulgaria on Monday.
The visitors went in front after just five minutes when Kane's cushioned pass sent Raheem Sterling speeding in behind the Czech defence and as the Manchester City forward cut inside, he was brought down by Lukas Masopust.
From the resulting penalty, Kane confidently slotted home for his 27th international goal and seventh in qualifying.
However, rather than going onto showcase why they will be among the favourites to win Euro 2020 with an abundance of attacking talent and home advantage on their side for most of the tournament, England showed the defensive frailties that could easily cost them next summer.
The hosts, ranked 44th in the world, caused problems for the World Cup semi-finalists all night and could even have been level before Brabec's equaliser as Jordan Pickford made a stunning save to deny Vladimir Coufal.
From the resulting corner, Southgate's side were found wanting twice as Ondrej Celustka won the first header and Brabec bundled the ball in at the back post.
The break gave Southgate a chance to reshape his midfield but still England could not gain control of the game despite creating more chances.
Sterling should have scored after being played in again by Kane, but tried to round Tomas Vaclik and the Sevilla goalkeeper parried the ball to safety.
Moments later, England were thankful to a brilliant stop by Pickford to prevent Masopust's dipping effort flying into the top corner.
Pickford was soon forced into action again to turn Alex Kral's driven shot behind at the near post.
But the Everton goalkeeper was helpless when Masopust broke down the right and crossed for Ondrasek to seal a famous victory.