Liverpool out of Europa League

Five-times European champions Liverpool were bundled out of the UEFA Europa League at the last-16 stage after failing to overturn a first-leg deficit against Sporting Braga.

The Portuguese side clung on for a goalless draw at Anfield which earned them a 1-0 aggregate victory courtesy of Alan's penalty winner in Portugal a week ago.

On a bad night for British clubs in Europe, Manchester City were also eliminated despite a 1-0 home win over Dynamo Kiev, while Rangers went out with a 1-0 loss to PSV Eindhoven.

Kenny Dalglish's men put up another poor show with Glen Johnson and Joe Cole having the best early chances, but Alan coming closest to breaking the deadlock for Braga with a 58th-minute miss.

Meanwhile City were hampered by Mario Balotelli's 36th-minute sending-off as they failed to overturn their 2-0 first-leg deficit at the City of Manchester Stadium.

Balotelli was issued a straight red card for a crashing challenge on Goran Popov and although Aleksandar Kolarov opened the scoring three minutes later with a free-kick, it was not enough.

Having done the hard work with a goalless draw in Holland, Rangers were eliminated by a 14th-minute tap-in from Jeremain Lens at Ibrox. PSV largely dominated with Balazs Dzsudzsak also hitting the woodwork.

Spartak Moscow hammered Ajax 3-0 at the Luzhniki Stadium to wrap up a 4-0 aggregate win with a free-kick from Brazilian Alex adding to first-half strikes from Dmitri Kombarov and Welliton.

Spartak, who had suffered an embarrassing 4-0 loss at Rostov in their Russian League opener on Monday night, dominated, although Christian Eriksson hit the bar for Ajax and was also denied by Spartak keeper Andriy Dikan.

Reigning Russian champions Zenit St Petersburg staged a heroic comeback bid at home to FC Twente but their 2-0 win on the night was not enough and they slid to a 3-2 aggregate defeat.

Roman Shirokov and Alexander Kerzhakov gave Zenit hope with first-half strikes, but Twente defended well and ought to have put the game out of Zenit's reach when Oguchi Onyewu missed a fine chance late on.

There was more Russian woe in Portugal, where Porto's 2-1 win over CSKA Moscow gave them a 3-1 aggregate success. Hulk and Freddy Guarin scored early before Zoran Tosic replied for the visitors.

Benfica joined Portugal in the last eight after a 1-1 draw in France gave them a 3-2 aggregate win over Paris St Germain. Nicolas Gaitan opened the scoring for Benfica on 27 minutes and Mathieu Bodmer's 35th-minute equaliser was not enough.

Villarreal wrapped up a 5-3 aggregate success over Bayer Leverkusen with a 2-1 home win. Santiago Cazorla and Giuseppe Rossi put the game beyond the Germans' reach before Eren Derdiyok's late consolation.