Five-time champions Liverpool made an early exit from the UEFA Champions League on Tuesday evening, while holders Barcelona saw off Inter Milan to put themselves in a strong position in Group F.

The English giants beat Debrecen 1-0 but were condemned by Fiorentina’s 1-0 defeat of Lyon, a result that sent the Italians through. Arsenal saw off Standard Liege 2-0 to also advance to the first knockout round, with Bordeaux, Chelsea, Lyon, Manchester United, Porto and Sevilla having already secured their places.

The results

Group E
Debrecen 0-1 Liverpool
Fiorentina 1-0 Lyon

Group F
Rubin Kazan 0-0 Dynamo Kiev
Barcelona 2-0 Inter Milan

Group G
Rangers 0-2 Stuttgart
Unirea Urziceni 1-0 Sevilla

Group H
AZ Alkmaar 0-0 Olympiacos
Arsenal 2-0 Standard Liege

The big game
Barcelona 2-0 Inter Milan
Goals: Gerard Pique 10, Pedro Rodriguez 26

The disappointing Italians were no match for a Barcelona side that recovered their poise in front of a packed Camp Nou. The defending champions could even afford the luxury of keeping Lionel Messi and Zlatan Ibrahimovic on the bench and saving them for Sunday’s clásico against Real Madrid.

Gerard Pique snaffled Barça’s opener after Thierry Henry had flicked on Xavi’s corner at the near post. The second came when Dani Alves clipped a perfect cross into the path of the unmarked Pedro, who sidefooted the ball past Julio Cesar from close range. With the visitors powerless to exert any pressure and former Azulgrana idol Samuel Eto’o making little impression, the Catalans were content to maintain possession thereafter as they moved to the top of the section and within touching distance of the next phase.

The surprise
Unirea Urziceni 1-0 Sevilla
Goal: Ivica Dragutinovic 45 og

Outplayed for most of the evening, the Romanians enjoyed a stroke of luck when Dragutinovic nodded a seemingly aimless free-kick past the startled Javi Varas in the Sevilla goal. Gratefully accepting the gift, the Group G outsiders then clung on to their lead to boost their chances of advancing to the last 16.

The other games
Fiorentina’s 1-0 defeat of Lyon in Florence took them to the top of Group E and into the next round. Juan Manuel Vargas scored the only goal of the game from the spot, just reward for La Viola’s domination. Though Les Gones managed to create some late pressure, the equaliser eluded them. That result was bad news for Liverpool, who won 1-0 at Debrecen thanks to David Ngog’s early goal but were condemned to a place in the UEFA Europa League. Uninspiring throughout the campaign, the Reds were left to rue their missed opportunities.

In the other match in Group F Rubin Kazan and Dynamo Kiev played out a goalless draw in some typically Russian winter conditions. Alejandro Dominguez came closest to breaking the deadlock when his superbly executed bicycle kick forced a brilliant save from Dynamo keeper Olexandr Shovkovskiy. The stalemate still leaves both sides in with a chance of qualifying.

Stuttgart enjoyed a profitable evening’s work when they outclassed Group G rivals Rangers at Ibrox Park, handing the Scots their third defeat in their three home games. The 2-0 win kept the Germans in the hunt for second place, which will be theirs if they can beat revelations Romanian Unirea at home on Matchday 6.

In Group H Arsenal made absolutely sure of their ticket to the last 16 with a comfortable 2-0 defeat of Standard Liege. Making a timely return following Robin van Persie’s injury, Samir Nasri set the Londoners on their way with a neat finish before Denilson doubled the Gunners’ lead with a 30-metre piledriver. Over in the Netherlands, second-placed Olympiacos were held to a 0-0 draw by Alkmaar and now require a point at home to Arsenal in their final game to go through.

The stat
2 - The number of times that Liverpool have now been knocked out in the group phase since the new competition format was introduced. The Merseysiders last came up short in 2002/03, when they trailed in third behind Valencia and Basle.

Goal of the night
Glasgow Rangers 0-1 Stuttgart (Sebastian Rudy 16)

Zdravko Kuzmanovic and Aleksandr Hleb combined to perfection on the left flank, working a gap in the Scots’ defence with a textbook one-two. Hleb’s cutback was then backheeled on by Pavel Pogrebnyak, with Sebastian Rudy arriving at the far post to tuck the ball home and complete a scintillating move.

Key Matchday 6 encounters

Group F: Inter Milan will qualify if they beat Rubin Kazan at home, an outcome that will also send Barcelona through, no matter how they fare against Dynamo Kiev in Ukraine.

Group G: Nothing less than a win will do for Stuttgart when they entertain Unirea Urziceni.

Group H: Olympiacos need a point at home to group winners Arsenal if they are to keep their Champions League adventure going.

Have your say
Having already won at Barcelona, can Russian champions Rubin Kazan pull off another shock at the San Siro in a fortnight’s time?