A limp England suffered their first qualifying defeat in over 10 years as Czech Republic came from behind to win 2-1 in Prague in European Qualifying Group A.
Level at 1-1 after a sloppy performance, England were punished by 30-year-old Czech debutant and substitute Zdenek Ondrasek, who converted low and unmarked from 10 yards to stun Gareth Southgate's side (85).
Group A table
England had taken an early lead through Harry Kane's penalty after Raheem Sterling was tripped (5), but the Czechs reacted immediately through Jakub Brabec, turning up at the back post after suspect England defending from a corner (9).
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The visitors were under par in the first half, failing to create any chances and allowing the Czechs several half-chances from set pieces, and though they improved after the break, England left with no points thanks to Ondrasek's winner.
A win would have sent England to Euro 2020, but defeat means England and Czech Republic are level on points at the top of Group A, with Kosovo four points behind.
England: Pickford (7), Trippier (5), Keane (4), Maguire (5), Rose (5), Rice (4), Henderson (5), Mount (6), Sancho (6), Sterling (6), Kane (7)
Subs: Barkley (7), Rashford (5)
Man of the match: Harry Kane
How England lacked class at both ends
Having been faultless defensively in European Qualifiers before a topsy-turvy 5-3 win over Kosovo last month, the chaos in England's back line continued in Prague.
But it started perfectly. Checking back at lightning speed in the box, Sterling was tripped by Lukas Masopust, allowing Kane to slot comfortably home from the penalty spot.
The 3,700 travelling England fans were in fine voice, but there were murmurs of discontent from then on. Thirty-six per cent of goals conceded by England under Southgate have been from set pieces (12/33), the latest coming from a corner as Ondrej Celustka's capitalised on Michael Keane's slip to find Brabec to bundle home from close range.
England did not react, and nor did they learn from their mistakes from the dead ball. Soucek rose above Declan Rice in an identical move to the equaliser, but Schick this time turned over from a tight angle, as England conceded over 10 shots in the first half of a game for only the second time in 78 matches.
On the ball, England did not look like the side 40 places above their opponents in the FIFA world rankings. Most of the first half was played in front of the Czech defence, Sterling was forced deep and wide, while both Jordan Henderson and Rice routinely misplaced their pass.
There were three changes from the win over Kosovo with Mason Mount making his first start for his country at the expense of Ross Barkley.
Kieran Trippier returned after being left out all together of the last squad, getting the nod over Trent Alexander-Arnold, while Danny Rose started ahead of Ben Chilwell.
There was no Callum Wilson in the squad due to illness.
After the break, England's passing initially emulated the first half, before Kane's fine through ball found Sterling one-on-one, only to be blocked by goalkeeper Tomas Vaclik as he looked to round him.
Masopust then forced Jordan Pickford into a fingertip save from range, and Southgate began changing things up with 18 minutes remaining as Marcus Rashford and Ross Barkley replaced Jadon Sancho and Mason Mount.
On his first start, Mount's 72 minutes were fine. At the time of his departure, he had the highest pass accuracy in the opposition half (87.5 per cent), the most key passes (2), but won just over a third of his duels and had only 27 touches.
The winner came from more poor England defending as Masopust's cut back found Ondrasek unmarked, allowing him to drive low to Pickford's left with a controlled effort. Tammy Abraham was introduced to save the day, but the day was one to forget.
Defeat seemed unthinkable before the game given England's superb record in qualifying, but their lack of class at both ends warranted nothing. They may now be made to sweat to make next summer's tournament in a group that could become messy.
Speaking to Sky Sports, England manager Gareth Southgate said his side had some time to go before being considered an elite team, and insists this reality check comes at the right time.
When asked if this result was a reality check, Southgate said: "Yes I think so.
"We are always very realistic about where we sit. We have an exciting team that usually look like scoring goals. We know there is a long way for us to go to become one of the top teams in Europe. We've got to respond to that performance on Monday and accept any criticism that comes our way."
Analysis: Poorest performance under Southgate
Sky Sports News' Rob Dorsett in Prague...
'That was as poor a performance as I can remember from an England team under Gareth Southgate. To a man, they looked out of sorts. For the first time in five qualifiers, England's usually razor-sharp attack looked decidedly blunt.
'Remember, before tonight, in each of England's four qualifying matches, they'd scored at least four goals. Here, they created very little, never tested Tomas Vaclik in the Czech goal, and despite the perfect start, there was an uncharacteristic lack of composure and creativity throughout the side.
'Even more worrying were the lapses in defence - lapses that pre-date tonight's game. They were there for all to see against Kosovo last month, when England were outplayed in the second half and conceded three goals.
'That will be a real concern for Southgate, as will England's increasing vulnerability to set pieces. It was a corner that led to Czech Republic's first goal, and they could have conceded more here from dead-ball situations.
'In fact, but for three top-class saves from Jordan Pickford, this would have been a much more comfortable victory for the home side. Up until now in qualifying, England's defensive frailties have been overshadowed by England's brilliance going forward. But not in Prague, where they were found out.
'England will still qualify for next summer's Euros. In fact, they could still qualify on Monday night with a win in Bulgaria. But Southgate has much to ponder, especially in how to sort out his mistake-laden defence.'
Roy Keane speaking on ITV...
'To me, there was almost a bit of arrogance from England. Sometimes you have to lose to win, as long as you're learning your lessons.
'But what I've seen from this team over the last year, and there's no need to panic, but they don't seem to be learning from those sloppy mistakes. Against a better team, you will suffer for it.
'There's no need to panic, Gareth's record has been outstanding. But my concern always for these players, is that I think sometimes these players don't learn. You can't keep waiting for these lads.
'Rose gave a performance tonight, my goodness, someone has got to get hold of that guy. Shocking, abysmal. I think he'll be the same in another three or four years, some players don't learn from their mistakes, and you will suffer for it.'
- Czech Republic had 17 shots in this match, the most England have faced in a qualifying match since March 2013, when Montenegro had 19 in a World Cup qualifier.
- Harry Kane has scored 20 goals in 21 matches for England when starting as captain - the only player with more is Vivian Woodward (23 goals between 1908 and 1911).
- Gareth Southgate (W21 D9 L8) has lost as many games as England manager in 38 matches as Roy Hodgson lost in 56 matches as manager (W33 D15 L8).
England now go to Bulgaria in Sofia on Monday night at 7.45pm, which you can follow on SkySports.com and the Sky Sports app, while Czech Republic host Northern Ireland in a friendly on Monday at 6pm, live on Sky Sports Football and Main Event.