European champions Liverpool crashed out of the Champions League on Wednesday at the hands of Benfica, leaving Arsenal as the only English representatives left in this year's tournament.
A goal down from the first leg of their last 16 tie, the defending champions slipped to a 2-0 defeat at Anfield.
By contrast, Arsenal moved into the quarter-finals after a 0-0 draw at Highbury against Real Madrid gave them a 1-0 aggregate win.
Simao -- a player that Liverpool came within hours of signing last summer -- grabbed the vital first goal in the 36th minute at Anfield with a wonderful curling left-footed drive which flew past Jose Reina in the Liverpool goal.
Liverpool twice hit the woodwork in the first half through Peter Crouch and Jamie Carragher while Benfica's Geovanni also had an effort come back off the crossbar.
Crouch and Luis Garcia also missed golden chances in the first half for the champions.
As the second half minutes ticked away, Liverpool found themselves needing to repeat the miracle of Istanbul last year when they score three goals on the way to winning the final.
But Benfica had the last word when Fabrizio Miccoli scored again a minute from time.
"Simao showed why he is such a good player," said Liverpool boss Rafael Benitez. "He plays with pace, he plays deep."
The statistics tell a depressing story for Liverpool.
Their four main strikers have managed just one goal between them in 45 matches.
"If you analyze the game, you can see that we created chances but when we conceded a goal, we had to go forward and we had to play with three defenders. That let them play on the counter-attack," said Benitez.
Arsenal, defending a 1-0 first leg lead, could have been ahead at the break had Juan Antonio Reyes not had a shot come back off the bar.
Raul was also denied by the woodwork on the hour mark while his follow-up was brilliantly kept out by goalkeeper Jens Lehmann but Arsenal held on to reach the last eight.
"We are very proud to represent England, the Premiership with dignity, with style and we will fight as hard as we can in the quarter-finals to go through again," said Arsenal boss Arsene Wenger.
Real's David Beckham said his team had done all they could have done to overturn Thierry Henry's first leg strike.
"I don't think we could have thrown anything more at them. They defended exceptionally well and we just couldn't break them down. I expected a few goals, but overall I wish them good luck because they are a good team," Beckham said.
AC Milan, last year's runners-up to Liverpool, booked their place in the last eight thanks to a 4-1 win over Germany's Bayern Munich.
Level at 1-1 after the first leg, Filippo Inzaghi gave Milan an eighth minute lead before skipper Andriy Shevchenko made it 2-0 on the night.
The Ukrainian striker also missed a first half penalty but quickly made amends with his 25th minute strike.
Valerian Ismail then gave Bayern a glimmer of hope pulling a goal back in the 35th minute before Inzaghi added a third two minutes after the break.
But Milan stepped up the pressure and Kaka made it 4-1 on the night on the hour.
Inzaghi refused to accept all the praise for Milan's passage into the last eight.
"I'm fortunate to play for a fantastic team and it's wonderful to see Milan play this way," he said.
Former Liverpool boss Gerard Houllier avoided the fate of his successor at Anfield, Benitez, by guiding French champions Lyon into the last eight.