| Liverpool suffered their first European defeat of the season as they were beaten 1-0 by Braga in the Europa League last 16, first-leg tie on Thursday night.
The home team got the only goal of the evening in Portugal on 18 minutes with Alan comfortably beating Pepe Reina from the penalty spot after Sotirios Kyrgiakos had brought down Mossoro in the area.
Liverpool struggled to muster a response and though Andy Carroll's introduction as an early second-half substitute did inject new life into their play, Braga were able to see out the contest to clinch the win.
The Reds departed John Lennon airport on Wednesday afternoon aiming to build upon Sunday's comprehensive 3-1 victory over Manchester United, knowing they would have to do so without the services of Steven Gerrard and Luis Suarez.
The captain remained behind on Merseyside to have a groin injury assessed, and though Suarez did travel with the squad, his appearances for Ajax in the competition earlier this season ruled him out of action.
Carroll was available for selection having made his long-awaited bow against United. However, with Kenny Dalglish eager to continue to err on the side of caution with his fitness, the club's record signing had to make do with a place amongst the substitutes.
Instead, the boss deployed Dirk Kuyt in attack with Raul Meireles operating just behind Sunday's hat-trick hero. There was also a start for Jay Spearing in an unfamiliar right midfield berth.
Maintaining an unbeaten record in European competition this season was added incentive for Liverpool as they kicked-off at the Estadio AXA.
Draws in each of their last four matches away from home in Europe had contributed to that sequence, and the opening exchanges were played out in tentative fashion, with the goalkeepers rendered largely unemployed.
But Braga were presented with an opportunity to open the scoring in the 18th minute when Kyrgiakos's ill-timed challenge on Mossoro gifted the hosts with a penalty.
Alan did the honours, converting beyond Pepe Reina with a powerfully-struck kick low to the Spaniard's right.
Liverpool were struggling to get out of first gear. Indeed, their first attempt of any note did not arrive until the 27th minute when Raul Meireles cannoned a free-kick against the wall from distance.
Braga, on the contrary, had been visibly buoyed by their opener - and they should have extended their advantage seven minutes before the break.
Hugo Viana's intelligent free-kick from the right took the Reds by surprise, allowing Mossoro a clear strike at goal from 10 yards. He could only fire his attempt against Kyrgiakos, but the Portuguese side worked the ball back to Silvio 30 yards from goal.
The full-back opted for a first-time volley, which beat Reina but crashed against the crossbar and to safety to ensure the teams headed into half-time with Braga holding only a one-goal lead.
A much-improved second-half showing was the order of the day for Dalglish's men, and there was certainly a degree of extra urgency in their play after the break.
Chances remained elusive, prompting Dalglish to summon Carroll from the bench at Christian Poulsen's expense 12 minutes into the second half to make the 22-year-old the 32nd player we've used in Europe this season.
It was a decision that almost paid instant dividends, with the striker heading over from a Meireles corner before having an effort deflected over the bar by Silvio.
Liverpool went closer still in the 67th minute when Kuyt chested down Joe Cole's right-wing cross on the edge of the box before scooping narrowly over Artur's crossbar.
Back came Braga and Viana almost caught Reina unawares with an in-swinging corner that the custodian was forced to palm into touch.
The visitors continued to toil in search of an away goal as the game headed to it's conclusion, but their endeavours ultimately proved to be in vain.
However, with Braga's advantage a slender one, Liverpool will be hopeful of toppling the deficit in next week's Anfield return.
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