A poor defensive performance saw Wales fall to defeat against the world's 96th-ranked team, Montenegro.
Danny Gabbidon, back for Wales after 18 months out injured, conceded a penalty, converted by Stevan Jovetic.
Rob Earnshaw had chances to bring Wales level, but on the stroke of half-time Simon Vukcevic's pass exposed Gabbidon and Radomir Djalovic finished superbly.
Replacement Sam Vokes scored with a powerful header from a Sam Ricketts cross, but that was Wales' last chance.
The friendly clash in Podgorica was the first between the two countries, following Montenegro's securing of independence from Serbia in 2006.
Wales, warming up for next month's World Cup qualifying clash with Russia in Cardiff, took the field wearing armbands for a cancer charity to show their support for former striker John Hartson, who is undergoing chemotherapy.
The lively Earnshaw had the goal in the net in the first minute, only to be pulled back for a foul.
It was Montenegro who had the first genuine chance, with Wales keeper Wayne Hennessey saving well from Savo Pavicevic.
A touch of class from Arsenal midfielder Aaron Ramsey set up Earnshaw's fellow front man Simon Church for a spectacular volley that flew just wide, the move earning warm applause from a sporting crowd at the Gradski Stadium.
The visitors were holding the ball well and frustrating Montenegro, who responded with some physical, niggly challenges.
Joe Ledley and Ramsey combined superbly down the right, skipper Ledley surging into the box only to blaze his shot high and wide.
But there were signs of slackness in a Wales defence that featured the return of West Ham centre-backs Gabbidon and James Collins after long-term injuries.
Jovetic fired straight at Hennessey, then launched a fine cross from the left that was headed over by Djalovic.
Gabbidon positive despite defeat
Gabbidon then got on the wrong side of his man, Vukcevic going down under his challenge.
The Serbian referee somewhat harshly awarded a penalty, and Jovetic sent Hennessey the wrong way.
Earnshaw did his best to get Wales level with a superb turn and break down the left.
With Church screaming for the ball in the centre Earnshaw chose to go for goal, but keeper Vukasin Poleksic closed the angle well.
Earnshaw had two more chances, including a spectacular overhead kick, but it was the home side who struck on the stroke of half time.
With an off-the-pace Gabbidon again out of position, Vukcevic slid through a beautiful ball from the edge of the box, Djalovic latching on to the pass and cutting the ball back across a helpless Hennessey for the second.
Toshack disappointed with defeat
Wales manager John Toshack brought on Lewis Price, Lewin Nyatanga and Vokes for Hennessey, Ashley Williams and Church at the break.
The change up front soon paid off, Ricketts looping a cross from the left that Vokes leapt for.
Although he was falling backwards, the Wolves striker got power and purchase on a header directed to the bottom corner, leaving replacement Montenegro keeper Mladin Bozovic no chance.
The outstanding Jovetic came close to restoring a two-goal advantage, breaking down the left before beating Price with a chip.
But the shot rebounded off the post into the keeper's back, bouncing out to Djalovic who blazed his snap effort wide.
Jovetic again went close after a lax Ramsey gave away possession in midfield, while the home side's aggressive approach continued, Miodrag Dzudovic booked for a shocking lunge at Earnshaw.
Wales faded under the challenge in a tame ending, and will hope that regular captain Craig Bellamy will be back to add experience and bite against Russia.
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