(CNN) -- Cristiano Ronaldo won his 99th international cap for Portugal -- but the Real Madrid superstar could not inspire his country as it slumped to a World Cup qualifying defeat in Russia.
Only Luis Figo (127) and Fernando Couto (110) have made more appearances for Portugal than Ronaldo, who will hope to reach his century against Northern Ireland on Tuesday.
Ronaldo had scored eight goals in his previous three games for Real Madrid, including a classy double against Barcelona in last Sunday's El Clasico.
But he was unable to prevent Russia from claiming a third consecutive victory in Group F to claim top spot as Fabio Capello's men recorded a 1-0 win.
Alexander Kerzhakov's sixth minute strike was enough to secure Russia its first ever win over Portugal in the post-Soviet era.
Playing on the synthetic surface at Moscow's Luzhniki Arena, Portugal struggled to make a breakthrough against a stubborn Russian defense.
Russian keeper Igor Akinfeyev made two impressive saves to deny Ronaldo and Bruno Alves as the visitors pushed for an equalizer.
But the home side held out and might have even extended their lead further had Denos Glushakov and Roman Shirokov made the most of their opportunities.
"I can't say that we looked bad tonight," Portugal manager Paulo Bento told AFP.
"In general we played a good match. We reacted well on the goal we conceded and we followed the plan which we worked out before the match.
"Of course Russia played a great match but I think the result wasn't fair as I know my team is capable of playing top quality football. We came here to win and are really upset now."
Germany underlined its credentials as potential World Cup winners with a 6-1 thrashing of the Republic of Ireland in Dublin.
The defeat, Ireland's heaviest at home since 1931, came with the hosts missing several key players including captain Robbie Keane.
Marco Reus scored twice in eight minutes to give the Germans a 2-0 lead at the break, before goals from Mesut Ozil, Miroslav Klose and two Toni Kroos strikes left Ireland decimated.
Andy Keogh grabbed a consolation for Ireland but that failed to tarnish a Germany performance which sees them top Group C with maximum points.
Germany has not lost a World Cup qualifier in its past 16 matches with its last defeat coming against England in September 2001.
World and European champions Spain eased to a 4-0 win in Belarus courtesy of a hat-trick from Barcelona's Pedro.
Jordi Alba gave the visitors a 12th minute lead before Pedro stole the show with a classy treble to wrap up victory in the Group I encounter.
France warmed up for Tuesday's World Cup clash with Spain by losing its friendly match 1-0 to Japan in Paris.
Shinji Kagawa's 88th minute strike stunned the home crowd and left the French cursing an embarrassing defeat.
Wayne Rooney moved up to fifth place in the list of England's all-time leading goalscorers after netting twice in a 5-0 win against minnows San Marino.
Rooney, who took his tally to 31 goals for his country, scored a goal in each half with his Manchester United teammate Danny Welbeck also notching twice.
"There are some great players there and to be in the England top five is something to be proud of," he told ITV1. "I am only 26 so hopefully I will score a lot more.
"We created some good chances and maybe there was a bit of poor finishing but it's not that easy when they put 10 or 11 men behind the ball.
"It's difficult to break them down and we had to create chances and we managed to do that, so obviously we'll take the positives and it wasn't a bad result."
Arsenal's Alex Oxlade-Chamberlain grabbed his first international goal to complete a routine win over a San Marino side ranked 207th out of 207 in the world rankings.
But there was bad news for Arsenal's Theo Walcott, who was taken to hospital for scans after being injured in a clash with San Marino goalkeeper Aldo Simoncini early on.
Italy was made to fight all the way in Yerevan before escaping with a 3-1 win over Armenia in Group B.
Henrikh Mkhitaryan had canceled out Andrea Pirlo's penalty kick to bring the hosts level, before second half strikes from Daniele de Rossi and Pablo Osvaldo secured victory for Italy.
Sweden survived an embarrassing episode against the minnows of the Faroe Islands after recovering to sneak a 2-1 win in Group C
Rogvi Baldvinsson fired the Faroes ahead after 57 minutes to leave Sweden facing a monumental World Cup qualifying defeat against a team ranked 131 places below.
Fulham midfielder Alexander Kacaniklic grabbed an equalizer before Zlatan Ibrahimovic bagged a 75th minute winner.
Netherlands recorded a third consecutive victory with a comfortable 3-0 win over Andorra.
Rafael van der Vaart, Klaas-Jan Huntelaar and Ruben Schaken were on target as the Dutch made it nine points out of nine in Group D
They sit top of the group alongside Romania, which also has maximum points from its three games following a 1-0 win in Turkey.
Belgium recorded a superb win after inflicting Serbia's first competitive home defeat since April 2001.
The Belgians cruised to a 3-0 victory in Group A with goals from Christian Benteke, Kevin De Bruyne and Kevin Mirallas.
Croatia sits joint-top on seven points with Belgium following a 2-1 win over Macedonia.
Tottenham star Gareth Bale scored twice, including a stunning left-footed rocket, as Wales came from behind to defeat Scotland 2-1 in Group A.