Russia 2-1 Wales
Pavel Pogrebnyak's late winner broke brave Welsh hearts in Moscow as the Russian replacement saved his side in their 2010 World Cup qualifier.
Roman Pavlyuchenko broke the deadlock for Russia from the penalty spot just minutes after Wales teenage sensation Gareth Bale had a penalty saved.
Joe Ledley's second-half strike stunned Russia to give John Toshack's rookie team hope of an unexpected draw.
But Pogrebnyak struck in the final ten minutes in the Lokomotiv Stadium.
Wales went within a whisker of being party poopers in Moscow as an intimidating and partisan crowd crammed into the compact ground to give their returning Russian heroes a warm welcome on a cold night.
It was Guus Hiddink's men first game back home since their Euro 2008 semi-final exploits in Austria and Switzerland and Pavlyuchenko almost gave the crowd something to cheer about as early as the tenth minute.
Tottenham Hotspur's new £14million striker let fly from 25 yards but his hit was deflected over by Wales centre-back Craig Morgan.
The Russian superstar got a little closer a few minutes later when the unmarked hitman volleyed Aleksandr Anyukov's pin-point cross goal wards.
But the 26-year-old was superbly denied by young Wolves goalkeeper Wayne Hennessey who palmed out his stinging shot before Ashley Williams hacked the loose ball to safety.
Despite Russia's domination, Wales - minus attacking talismen Craig Bellamy and Jason Koumas - enjoyed sporadic attacking sorties.
And when Gareth Bale burst into the box from Joe Ledley's flick, the Spurs full-back was sent tumbling by Russia skipper Sergei Semak.
The £10m man's fall was a little theatrical but referee Damir Skomina wasted little time in pointing to the spot.
Bale dragged himself up off the turf but the 19-year-old's left-footed penalty was a good height for Igor Akinfeev and the Russia stopper made a fairly routine 17th minute save.
Wales' second spot-kick nightmare in successive matches was punished almost immediately as Bale's new Spurs team-mate Pavlyuchenko showed him how it should be done.
Russia's chance to the break the deadlock was down to a comedy of Welsh defensive errors as Morgan's misplaced back-header was perhaps naively kept in by Wales keeper Hennessey.
Pavlyuchenko pinched the ball from Hennessey and teed up the busy Yuri Zhirkov who was clattered to the ground by a clumsy Carl Robinson challenge.
Referee Skomina again pointed to the spot and Pavlyuchenko was coolness personified as he chipped the ball above the despairing dive of Hennessey, whose touch was not enough to prevent Pavlyuchenko scoring his tenth Russian goal.
Russia unleashed wave upon wave of attacks on a patched-up Welsh defence - without first-choice centre-backs Danny Gabbidon and James Collins - made up of inexperienced youngsters and lower league unknowns.
And they bravely held out as the supremely talented Andrei Arshavin and Pavlyuchenko looked to capitalise on Wales' lack of experience as the free-flowing Russians started to enjoy a party atmosphere in Moscow.
The movement of Russia's sublime strike-force was a joy to watch but a devil's own job to defend against - but the hosts lacked a cutting edge.
The injury-ravaged visitors gave Russia a few reminders of their potential danger as Joe Ledley found space in the box but failed to hit the target from Chris Gunter's deep cross.
Dave Edwards, too, gave Russia a scare after the break but his header from Gunter's searching cross was just too high.
But Pavlyuchenko was desperate to ensure he remained the centre of attention just days before his Premier League debut for his new employers.
Arshavin, the Russian striker that Tottenham failed to sign this summer, was just inches away from emulating his strike-partner.
The Zenit St Petersburg ace sprinted free in the penalty area but couldn't keep his header from Auyukov's delicious inswinging cross down.
Wales' heroic defence to stem the red Russian tide near Red Square paid off in the 67th minute as boss John Toshack's bravehearts snatched a shock leveller in the Lokomotiv.
Bale made amends for his earlier penalty blunder by skipping past two Russian defenders to tee-up Joe Ledley who stunned to masses in Moscow.
Bale drove into the box and Ledley, an FA Cup final hero with his beloved Cardiff City last season, tapped in Bale's wicked low right-wing cross into Akinfeev's net for his second Welsh goal.
Steve Evans created some post-war history when he replaced Edwards in the 77th minute as the Wrexham defender became the first non-League player to represent Wales for 78 years since the infamous 'unknowns' that played Scotland in 1930.
Sadly for spirited Wales, the Russian onslaught broke through with ten minutes remaining as substitute Pogrebniak saved Russian blushes.
Chris Gunter allowed Arshavin an inch and Russia's playmaker general delivered a tantalising cross that Konstantin Zyryanov brought the best out of Hennessey.
Unfortunately for Wales the rebound fell to Zenit St Petersburg man Pogrebnyak who rammed the ball home to seal a hard-fought Russian victory.