Japan conceded a last-minute goal to go down 2-1 to Bulgaria in Osaka.
Yanev celebrates his late winner
Substitute Hristo Yanev snatched a fortuitous winner in injury time with a 30-metre free kick that crept inside Yoshikatsu Kawaguchi's far post.
Portsmouth's Svetoslav Todorov had stunned the home support after just 53 seconds with a neat finish.
Japan, missing many big-name stars, found reward for their domination on 76 minutes when striker Seiichiro Maki turned in a fierce drive from Alex.
"I don't think we deserved to lose," said Japan coach Zico.
"I thought we played well but once again we failed to take our chances and we got punished for it."
After going behind home midfielder Yuki Abe forcing a tremendous save from Stoian Kolev and striker Keiji Tamada crashing a left-foot shot against the post.
"We were confident we could beat them. But of course it might have been a different game if Japan had had all their best players available," said Bulgaria coach Hristo Stoichkov.
Japan: Kawaguchi, Tanaka (Ogasawara 61), Miyamoto, Nakazawa, Murai (Santos 44), Kaji, Fukunishi (Ono 61), Endo, Abe (Hasebe 83), Tamada, Maki (Sato 77).
Subs Not Used: Doi, Narazaki, Tsuboi, Komano, Moniwa, Motoyama, Kubo.
Goals: Maki 76.
Bulgaria: Kolev, Stanislav Angelov, Topuzakov, Kirilov, Milanov (Valentin Iliev 46), Wagner, Martin Petrov (Yanev 86), Jankovich (Georgi Iliev 26), Telkiyski (Karaslavov 90), Svetoslav Todorov (Domovchiyski 63), Todarov.
Subs Not Used: Mihaylov, Genkov.
Goals: Svetoslav Todorov 1, Yanev 90.
Ref: Carlos Megia Davila (Spain).