Netherlands' hopes of qualifying for the 2018 World Cup were dealt a severe blow by a 2-0 defeat to Bulgaria as Matthijs de Ligt endured a debut to forget in Sofia.
At just 17 years of age, the highly-rated Ajax central defender was the youngest player to turn out for Oranje since 1931, but it was a painful introduction to international football for a man who had made just 14 senior appearances prior to Saturday's meeting, which marked the halfway point on the road to Russia.
In the build-up to this Group A clash, under-fire Netherlands coach Danny Blind conceded that De Ligt had only been called upon due to injuries to regular choices Virgil van Dijk, Jeffrey Bruma and Stefan de Vrij.
And De Ligt was culpable for Bulgaria's fifth-minute opener, his failure to deal with a long ball capitalised on by Spas Delev for his first Bulgaria goal.
Delev doubled his and Bulgaria's tally with a fine finish before the midway point of the first half, at the end of which De Ligt was replaced by Wesley Hoedt.
Despite an improved post-interval performance, Netherlands could not conjure a way back into the contest and after their failure to qualify for Euro 2016, their hopes of reaching Russia next year seem slim with Blind's side now fourth in the group, three points adrift of second-placed Sweden and six behind leaders France.
17y 225d - Matthijs de Ligt becomes the youngest player to play for the Netherlands since 1931 (Mauk Weber, 17y 222d). Rookie. — OptaJohan (@OptaJohan) March 25, 2017
It was a torrid outing for the visitors and De Ligt, whose nerves were evident within 15 seconds as he conceded a free-kick from which Ivelin Popov brought a save out of Jeroen Zoet.
But the respite was brief and the youngster was at fault for the opener, losing the flight of Simeon Slavchev's hopeful punt forward and allowing Delev to nip in, prod the ball past Zoet and tap home.
Netherlands struggled to gain a foothold in the game and things went from bad to worse in the 20th minute as Delev picked up Georgi Kostadinov's cushioned header, stepped away from De Ligt and arrowed a low strike into the bottom-right corner from 20 yards.
It took until the penultimate minute of the half for Netherlands to carve out a clear goalscoring opportunity and when it arrived Bas Dost stabbed wastefully wide from close range after Davy Klaassen had done brilliantly to keep the ball in play.
Quincy Promes tested Nikolay Mihaylov from distance just prior to the hour, the goalkeeper producing a much better save to deny Klaassen shortly afterwards.
But those glimpses of a potential fightback failed to materialise into anything concrete as Netherlands slipped below their hosts in the table and closer towards another absence from a major international tournament come June next year.