Liverpool slipped up against second division German opposition and finished their match against Kaiserslautern with goalkeeper Jose Reina in midfield.
An injury to Luis Garcia left boss Rafael Benitez with little option other than to press Reina into action in an unfamiliar position with 11 minutes left of a match being played in Liechtenstein.
And while Reina twice came close to scoring, shooting narrowly wide and then over the bar, it was Kaiserslautern who clinched victory thanks to Marcel Ziemer's strike in the 87th minute.
After a goalless first half, Craig Bellamy looked to have given Liverpool the lead soon after the re-start when his shot hit the bar and appeared to cross the goalline, however the decision went against the Welshman.
Liverpool handed a debut to Jermaine Pennant in the second half and he looked threatening, however the German side went in front after 56 minutes when substitute Ricardo Villar fired past Jerzy Dudek, making the most of an error by Jack Hobbs.
Bellamy got the goal he deserved on the hour mark following good work from another substitute, Luis Garcia.
It was Luis Garcia who shot Liverpool in front after 67 minutes, Pennant and Bellamy having made the opening for the Spaniard, however Kaiserslautern were level four minutes later.
Ziemer pounced on another Hobbs mistake to strike their equaliser.
Reina's introduction in place of Luis Garcia, who suffered a minor knock, almost brought about a dramatic result as his shots caused Kaiserslautern concern.
But Ziemer had the final say, finding space behind the Liverpool defence and lifting his shot above Dudek for the winner.
(re-opens) Benitez admitted the friendly match had not gone according to plan, and Liverpool must now wait not only for news of Garcia but also of defender Fabio Aurelio.
Aurelio, also a half-time substitute, was another who had to be taken off before the final whistle, and he could face several weeks on the sidelines with a calf injury.
Benitez told www.liverpoolfc.tv: "It was a difficult game for us with the two injuries to Luis and Fabio and we made three mistakes which cost us the game.
"Luis had a problem with his neck and we decided the best thing would be to take him off. Fabio felt something in his calf and I think it's a more serious problem than Luis."
If there was a positive to come out of the defeat, it was that Pennant performed well in his first appearance since signing from Birmingham.
"I thought Jermaine Pennant did a good job and played well," said Benitez. "He showed the quality that he has."
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