Liverpool suffered a 1-0 defeat at the hands of Braga in the first leg of their Europa League last-16 clash thanks to Alan's first-half penalty.
The Brazilian coolly slotted home from the spot in the 18th minute, after Sotirios Kyrgiakos had brought down Mossoro as he burst into the box.
The hosts continued to press their early advantage, and almost added a second through Silvio. After Salino's effort from Hugo Viana's corner failed to evade the Liverpool defence the ball bounced out to the young defender, who hit a beautiful left-footed volley from all of 30 yards that had Pepe Reina beaten before it crashed away off the crossbar.
After struggling for much of the first-half to create an opening of note, Liverpool looked significantly more threatening after the introduction of Andy Carroll shortly after half-time. But, while clearly a threatening presence in the air, the £35 million striker failed to find a breakthrough in the remainder of the game, with Glen Johnson's blocked free-kick as time expired summing up his side's blunt attacking edge throughout.
There was some late concern for Kenny Dalglish late on after Carroll was elbowed in the face by defender Kaka, who was lucky to avoid punishment. But, after needing treatment for a few minutes, the former Newcastle striker picked himself up to widespread relief.
Manchester City will have to dig themselves out of a hole at the City of Manchester Stadium after losing 2-0 to Dynamo Kiev in Ukraine.
Former Chelsea forward Andriy Shevchenko gave his side the lead in the 25th minute, reacting first inside the box to sneak in front of the onrushing Joe Hart and poke home Andriy Yarmolenko's low cross from the left.
With a disgruntled Roberto Mancini looking on throughout City did occasionally threaten, with Kiev goalkeeper Olexandr Shovkovskiy making a number of smart saves including notable ones to deny Yaya Toure and Joleon Lescott. But City did not always look sturdy defensively as the Ukrainians rushed forward, and they were made to pay as Oleg Gusev pounced on Artem Milevskiy's flick inside the box to take one touch and then volley a powerful right-footed shot beyond Hart and into the back of the net.
City pushed on search of a potentially vital away goal as the game neared its conclusion, leaving open gaps at the back that their opponents were eager to exploit. Gusev nearly grabbed his second late on but was denied by Hart's sprawling save, and Milos Ninkovic wasted a decent opportunity as Kiev showed they will be a counter-attacking force to be reckoned with in the second leg.
Paris St Germain let a 1-0 lead slip as they lost 2-1 away to Benfica in a result that will nevertheless give them a decent chance of progressing to the competition's quarter-finals.
Everything looked so healthy for the French side when Peggy Luyindula put them ahead inside the first 15 minutes, but Uruguayan international Maximiliano Pereira levelled the scores with his left-foot shortly before half-time.
With less than 10 minutes remaining, Franco Jara then found enough time and space on the left-hand side of the box to drive home a shot that will see his side take a slender advantage back to the French capital.
In the Netherlands, Rangers showed great resilience to hold PSV Eindhoven to a 0-0 draw. Despite dominating both the possession, the Dutch side never really looked like breaking down Walter Smith's side, with Antonio Morales and Marcus Berg both guilty of missing decent opportunities and lively Balazs Dzsudzsak failing to find a goal despite covering a lot of ground.
Twente gave themselves a healthy advantage against Zenit St Petersburg, winning 3-0 thanks to goals from Luuk de Jong and former Wigan Athletic midfielder Deny Landzaat, while Alex got the only goal, somewhat against the run of play, as Spartak Moscow grabbed both an away goal and a 1-0 victory against Ajax.
In Germany, Villarreal grabbed a last-gasp 3-2 victory against Bayer Leverkusen thanks to Nilmar's intervention deep into injury time.
Michal Kadlec opened the scoring for the hosts on the half hour mark but Giuseppe Rossi evened the score shortly before half-time with a low left-footed drive. Nilmar then put the Spanish side ahead with a beautiful turn and finish, but Gonzalo Castro took all of two minutes to find an equaliser with his right-footed finish from six yards out.
With the game looking like heading for a draw, the wily Brazilian then added his second with a quick finish in the fourth minute of injury time to send the Spanish side home with a crucial advantage.
In the night's other early kick-off, FC Porto grabbed a significant 1-0 first leg lead after a fine away win against CSKA Moscow. Midfielder Fredy Guarin found the only goal of the game in the 70th minute, thanks to a drive from the edge of the penalty area that eluded goalkeeper Igor Akinfeev.