Portuguese outfit Sporting Braga have produced a 1-0 result over Liverpool at Estadio AXA tonight.
Alan OsÃ³rioâ€™s 18th minute penalty was the difference between the sides in an otherwise mediocre clash with provided few clear-cut chances.
In Jamie Carragherâ€™s 138th appearance in Europe, a new British record, Liverpool were the more dangerous team in the second half but they could not find the back of the net and will have to try and overcome Domingos PaciÃªnciaâ€™s men in the return bout in a weekâ€™s time.
Uefa Europa League â€“ Round of 16 first leg
Sporting Braga (POR): 1 (Alan OsÃ³rio (p) 18â€™)
Liverpool (ENG): 0
Venue: Estadio AXA, Braga â€“ Portugal
Referee: Serge Gumienny (BEL)
Yellow cards: BRA - Claudio KakÃ¡ 24â€™
LIV - Christian Poulsen 33â€™
Neither side were doing any damage early as both goalkeeper had a simple start to proceedings until the 17th minute when Reds defender Sotirios Kyrgiakos brought down Mossoro in the area with referee ??? pointing straight to the spot.
GOAL The dreadlocked Brazilian Alan OsÃ³rio stepped up to the spot and hammered it past Pepe Reinaâ€™s right hand to notch up Bragaâ€™ 100th goal in European competition.
Liverpool were playing a patient type of game and it almost went against them when Bragaâ€™s SÃlvio crashed a 30-yard volley into the crossbar after having Reina well-beaten in the 35th minute which was the last chance of any note in the opening 45 minutes.
Kenny Dalglish then entered Andy Carroll into the fray just before the hour-mark and he made an immediate impact as the Reds were looking far more dangerous after his arrival.
Carrollâ€™s 63rd minute shot was deflected over the bar before Meireles picked out Dirk Kuyt who controlled with his chest before seeing his shot tipped over by Artur.
It seemed like the visitors would certainly grab a leveler until the home side started to again control proceedings with the Braga fans getting their voice back as the minutes ticked over.
The Reds were desperate to nick an away goal but were unable to pierce a strong Braga defence and will have to try and wrestle back control in the return leg at Anfield next week.
Artur Guilherme (gk) â€“ Miguel Angelo Garcia, Claudio KakÃ¡, Alberto RodrÃguez, SÃlvio Manuel â€“ Hugo Miguel Viana, Mossoro (PaulÃ£o 68â€™), Leandro Salino â€“ Alan OsÃ³rio, Paulo CÃ©sar Rocha (Barbosa 90+4â€™), Rodrigo Lima (ZÃ© Meyong 77â€™)
Subs - Cristiano Figueiredo (gk), PaulÃ£o (68â€™), Albert ZÃ© Meyong (77â€™), HÃ©lder Jorge Barbosa (90+4â€™), AnÃbal AraÃºjo, Coelho Dani, Peterson Joseph
Subs - PÃ©ter GulÃ¡csi (gk), Andy Carroll (57â€™), John Flanagan, Danny Wilson, Maxi RodrÃguez, David Ngog, Dani Pacheco