New signing Milan Jovanovic made a 45-minute debut for Liverpool as a largely inexperienced reserve side lost 1-0 to Kaiserslautern in Germany.
The Serbia forward, brought in on a free transfer from Standard Liege, played the first 45 minutes before he was withdrawn by manager Roy Hodgson.
By that time the Reds were behind, courtesy of Ilian Micanski's close-range tap-in.
Jovanovic was one of only two members of the squad who had played at the World Cup, the other being defender Sotirios Kyrgiakos who lasted 77 minutes.
The Greek almost made a perfect return to life in a Liverpool shirt as his second-minute through-ball put David Ngog in on goal but he dragged his shot wide.
Moments later the newly-promoted Bundesliga side replied with Slovakian Adam Nemec having a shot deflected just over.
The 19-year-old Liverpool reserve forward David Amoo then shot straight at Tobias Sippel and Martin Kelly had an effort deflected over from Jovanovic's corner before the hosts made the breakthrough.
In the 32nd minute Jiri Bilkey beat Daniel Ayala to the ball before crossing for Micanski to extravagantly flick home from six yards.
Croatian Ivo Ilecevic's volley went close five minutes before half-time as Kaiserslautern continued to press.
After the break the Germans created a couple of opportunities but Hodgson's youthful side - midfielder Lucas Leiva was the most experienced first-teamer - did not concede again.
Hodgson now prepares to start his competitive Reds career with a Europa League third round qualifier against Macedonians FK Rabotnicki on Thursday without many of his first-team stars.
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