England missed an opportunity to qualify for Euro 2020 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 Hotspur striker taking his qualifying tally to seven goals.
But Czech, 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 host on 85 minutes, a goal that ended England's decade-long unbeaten run in qualifying spanning 43 matches.
England's last qualifying defeat came ahead of the 2010 World Cup when they lost 1-0 away to Ukraine in October 2009.
Southgate's side remain top of Group A on 12 points alongside the Czechs, who have played a game extra.
??????? Harry Kane for England: ⚽️2⃣7⃣?4⃣2⃣#EURO2020 pic.twitter.com/7GWCCt0KiS
— UEFA EURO 2020 (@UEFAEURO) October 11, 2019
England could still clinch qualification Monday with victory in Bulgaria if Kosovo fail to beat Montenegro.
World champion 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.
Cenk Tosun popped up with a 90th-minute winner for Turkey as they scraped past Albania 1-0 in Istanbul.
Iceland's first home loss in qualifying since June 2013 dropped the Nordic island nation six points adrift of the top two.
??@UEFA Goals in 2⃣0⃣1⃣9⃣
— Twitugal? (@Twitugal) October 11, 2019
➡Clubs + National Team :
1. ??@Cristiano 15 Goals (+1⚽)
2. ??Giroud 12 Goals (+1⚽)
3. ??Sterling 11 Goals
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 visitor's defence.
Goncalo Guedes added a late third although defending champion Portugal still trail Group B leader Ukraine by five points.
Portugal next travel to Kiev to face a Ukraine side on the cusp of qualification following a 2-0 home win over Lithuania secured by 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 minnow 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.
RESULTS
Czech Rep 2 (Brabec 9, Ondrasek 85) England 1 (Kane 5-P)
Montenegro 0 Bulgaria 0
Portugal 3 (Bernardo 16, Ronaldo 65, Guedes 89) Luxembourg 0
Ukraine 2 (Malinovskyi 29, 58) Lithuania 0
Andorra 1 (Vales 63) Moldova 0
Iceland 0 France 1 (Giroud 66-P)
Turkey 1 (Tosun 90) Albania 0
