5 of the greatest Champions League Round of 16 upsets

3. A.S Roma 4 - 2 Real Madrid: 2007-08

Roma pulled off a great upset by beating Real Madrid over both legs in the 07-08 Champions League

Frustrated at the continued European disappointments during the Galacticos era, Real Madrid fans were relieved when they were placed against Italian giants but European minnows A.S Roma at the round of 16 stage of the 2007-08 Champions League.

Roma had never won the Champions League or the UEFA Cup and were expected to be easy pickings for Los Blancos, but the Giallorossi had steadily progressed under Luciano Spalletti over the past two years and had won the Coppa Italia the previous season. They also featured the reigning European Golden boot winner Francesco Totti in their ranks.

Real started brightly in Rome's Stadio Olimpico, racing to a 1-0 lead within the first eight minutes, but the famous 'Curva Sud' boosted the morale of the Italians and David Pizarro equalised by the 25th minute. After the break, Amantino Mancini scored to give Roma the advantage, which they protected until the final whistle.

Despite the setback, Real were still favourites to overcome the setback at the Santiago Bernabeu, considering that a 1-0 win would be enough to go through, but the one goal requirement suddenly became three as Rodrigo Taddei shocked Iker Casillas to give Roma the lead in the 73rd minute. Raul equalised minutes later, but the Romans were still ahead on aggregate.

Deep into injury time, desperate Real were further punished by a brilliant Roma counter-attack which culminated in Mirko Vucinic beating Casillas to give Roma a 2-1 win on the night and a 4-2 victory on aggregate.

It would be another three years before Real were finally able to break the 'round of 16 curse' at the Champions League.