Paris: England missed an opportunity to qualify for Euro 2020 on Friday as they slid to a 2-1 loss in the Czech Republic, while Cristiano Ronaldo scored his 699th goal in a routine Portugal win over Luxembourg.
Harry Kane converted a fifth-minute penalty in Prague after Raheem Sterling was clipped by Lukas Masopust, the Tottenham striker taking his qualifying tally to seven goals.
But Czech Republic, humbled 5-0 by England in the reverse fixture last March, levelled shortly after as Jakub Brabec bundled in from a corner for his first international goal.
Substitute Zdenek Ondrasek swept home the winner on his debut for the hosts on 85 minutes, a goal that ended England’s decade-long unbeaten run in qualifying spanning 43 matches.
Their last defeat came in a 1-0 World Cup qualifying loss against Ukraine in October 2009.
Gareth Southgate’s side remain top of Group A on 12 points alongside the Czechs, who have played a game extra. England could still secure qualification on Monday with victory in Bulgaria if Kosovo fail to beat Montenegro.
“Clearly that’s a night we did not want to be a part of. We didn’t play well enough, it’s as simple as that,” said Southgate.
“We’ve always maintained there is a lot of work to be done to be a really top team. Tonight was clear evidence of that.”
World champions France claimed a 1-0 win away to Iceland as Olivier Giroud delivered the only goal with a penalty on 66 minutes in Reykjavik.
Giroud has played sparingly for Chelsea this season but the 33-year-old is now just four goals behind Michel Platini (41) for second on France’s list of all-time leading scorers.
France are level on 18 points with Turkey atop Group H ahead of Monday’s showdown in Paris, where victory would send Didier Deschamps’ men through to the finals.
Juventus star Ronaldo grabbed his 94th goal at international level in Portugal’s 3-0 home victory over Luxembourg.
Bernardo Silva opened the scoring in Lisbon in the first half before Ronaldo added a second on 65 minutes with a magnificent chip following an error in the visitors’ defence.
Goncalo Guedes added a late third although defending champions Portugal still trail Group B leaders Ukraine by five points.
The two countries meet in Kiev on Monday. Ukraine will be hopeful of nailing down qualification following a 2-0 home win over Lithuania courtesy of Atalanta midfielder Ruslan Malinovskyi’s brace.
A goalless draw between Montenegro and Bulgaria eliminated both teams from contention in Group A, while it was a night to remember for Andorra.
The minnows won their first European qualifier in history after 56 defeats in a row as Marc Vales’ second-half header earned Andorra a 1-0 victory over 10-man Moldova.
Montenegro 0 Bulgaria 0
Czech Republic 2 England 1
Ukraine 2 Lithuania 0
Portugal 3 Luxembourg 0
Turkey 1 Albania 0
Iceland 0 France 1
Andorra 1 Moldova 0