Zdenek Ondrasek scored on his international debut as the Czech Republic handed England their first qualifying defeat in a decade on a disappointing night in Prague.
The Three Lions had gone 43 qualifying games in the World Cup and European Championships without tasting defeat, stretching back ten years, but they deservedly lost after a scratchy display in Prague.
Gareth Southgate's men enjoyed the perfect start as well, when Raheem Sterling's pace and quick feet won England a penalty, which Harry Kane dispatched for a fifth-minute lead.
Undeterred, Czech Republic came storming back and levelled before ten minutes had been played when Jakub Brabec stabbed home at the far post when England failed to clear a corner.
From there the pattern remained the same with the hosts looking far more comfortable on the ball while England looked edgy in possession, toothless up front and, far more worryingly, extremely nervous at the back especially at set pieces.
It was more sloppy play out from the back that handed the Czechs the chance to win it five minutes from time, and they made no mistake as the Lukas Masopust cut-back was pinpoint and the Ondrasek finish clinical as he marked his international debut with the biggest goal of his career.
Ondrasek, a second half substitute, was making his international debut at the age of 30, and the FC Dallas man managed to score the winner against England with his first shot in international football.
No facet of England's game was working well in Prague. Their defensive problems were there for all to see and both goals could have been avoided, but the midfield lacked both creation and ball retention, while the front three of Kane, Sterling and Jadon Sancho were easily marshalled.
It may just have been one of those nights but Southgate will be hoping the quick turnaround to Monday's game in Bulgaria will help his side to produce a response to one of the worst performances under his largely positive tenure.