Real Madrid 1 Roma 2 (agg 2-4): Nine-time winners Real Madrid have been knocked out of the Champions League in the second round for the fourth successive year after a 2-1 defeat to Roma at the Santiago Bernabeu.
Goals from Rodrigo Taddei and Mirko Vucinic either side of a Raul strike ensured safe passage for the Italians after Real defender Pepe was dismissed for a second booking in the 71st.
Taddei headed Roma in front two minutes later but Real clung on to some hope of forcing extra-time with a Raul equaliser in the 75th minute.
Raul was clearly a yard or two offside from Robinho's pass but after a 2-1 defeat in Rome his strike meant Real needed one more to bring the game to extra-time.
The homeside pressed in vain for the goal but all the while left themselves vulnerable to the swift counter-attacks of Taddei and Vucinic on the Roma flanks, and they were punished by the latter when he netted at the death.
Roma keeper Doni was not pressed into action until the 17th minute when he did well to deal with a deflected Julio Baptista free kick, but the Italians responded with two great shots that gave the Bernabeu a warning of what was to come.
Midfielder Alberto Aquilani sent a rasping drive slamming on to the bar from 20 metres out and Taddei followed up with another fierce shot that had Iker Casillas scrambling to turn past the post.
Without the injured Ruud van Nistelrooy, Real lacked bite up front and grew increasingly frustrated as they got no change from the miserly Roma back four.
Roma, in contrast, looked more and more confident as they clipped the ball neatly around the midfield and broke quickly into attack.
Real threatened once more at the start of the second half, Baptista smacking a dipping free kick against the bar and Mahamadou Diarra testing Doni with a powerful drive.
But once again it was Roma who came closest to breaking the deadlock when Vucinic rattled the bar with a thundering drive less than a minute after coming on.
Real began to lose their cool when Pepe was sent off after picking up a second booking for a foul on Vucinic and Taddei took advantage of the confusion in defence to head home two minutes later.
Raul hit back almost immediately, sweeping low past Doni after a neat through pass from Robinho but Roma dealt the definitive blow when Vucinic threw himself at a Christian Panucci free kick and headed in past Casillas.
In the night'sother game Schalke 04 beat FC Porto on penalties in Portugal after an 86th minute Lisandro Lopez goal overturned a 1-0 deficit incurred in Germany to send the game to extra-time.
Schalke goalkeeper Manuel Neuer was the hero, topping off a brilliant performance over two hours with two excellent saves from the spot.