A stoppage-time header from Iliyan Mitsanski saw Bulgaria snatch a surprise win in their friendly against Euro 2012 hopefuls Holland.
Oranje took the lead through Robin van Persie shortly before the interval at Amsterdam ArenA, but that was cancelled out by a penalty from Ivelin Popov.
A draw then looked the most likely outcome as the clock ticked down, but substitute Mitsanski popped up at the death to silence the home crowd.
It is a disappointing result for Bert van Marwijk's men, who will travel to Poland and Ukraine next month as one of the tournament favourites following their runners-up finish at the 2010 World Cup.
However, the win will do much for Bulgaria's confidence as they look to recover from a dismal European qualifying campaign which saw them finish last in their group.
Things did not start well for the hosts, who saw Joris Mathijsen replaced by Wilfred Bouma in midfield after the Malaga player was injured in the 17th minute.
Holland eventually settled down, though, and Wesley Sneijder gave Stoyan Kolev his first real test after 37 minutes with a 25-yard drive which warmed the palms of the goalkeeper.
A minute later, Sneijder was causing more problems with a free-kick which the Inter Milan midfielder curled inches over the crossbar.
Bulgaria had to wait until the 43rd minute for their opening chance and it almost broke the deadlock as Valeri Bojinov smashed the bar with his left-footed free-kick.
Instead, it was Van Persie who scored first, with Sneijder providing the cross for the Arsenal forward to fire into the bottom left corner a minute before the interval.
Bulgaria's reply arrived four minutes into the second half.
Rafael van der Vaart handled the ball in the area, giving away a penalty and picking up a booking for his troubles. Popov made no mistake with the spot-kick, calmly placing the ball into the bottom left corner.
Sneijder tried to get the subdued crowd going once more with a right-footed strike but Kolev was equal to the challenge.
Stanislav Manolev responded for the visitors with a right-footed volley after 69 minutes which only just missed the target.
Holland once again looked to Sneijder for inspiration 10 minutes from time, but the midfielder was denied by substitute goalkeeper Nikolay Bodurov, who had come on for Kolev eight minutes earlier.
Bulgaria had given a good account of themselves in the match and home keeper Tim Krul did well to turn away a left-footed drive from Vladimir Gadzhev five minutes from time.
However, a late lapse in concentration from the Holland defence allowed Mitsanski to meet Manolev's teasing cross and head home the winner from close range.