Wales' Euro 2012 qualification hopes suffered a crushing blow at Cardiff City Stadium after Ivelin Popov's second half strike gave Bulgaria a 1-0 victory.
Wales, under the control of caretaker manager Brian Flynn, created several chances and should have taken an early lead, but full-back Chris Gunter shot wide from inside Bulgaria's box.
And they were punished just three minutes into the second period when an unmarked Popov pounced to leave Wales floundering in Pool G, with Gunter sent off in injury-time for a bad foul on Dimitar Rangelov.
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