06/03/2013 04:32 GMT | Updated 05/05/2013 06:12 BST

Manchester United v Real Madrid: A Night Nani Will Want To Forget (PICTURES)

Manchester United were knocked out of the Champions League by José Mourinho's Real Madrid last night in Manchester. Utd lost 2-1 at Old Trafford after two quick strikes from the former Spurs midfield Luka Modrić and Cristiano Ronaldo.

The most controversial moment of the game came in the second half as Turkish referee Cuneyt Cakir dismissed Portuguese international Nani, when his boot caught Alvaro Arbeloa's chest as they went for a high ball, rightly or wrongly Nani was sent off.

Nani is sent off for Manchester United after a challenge on Alvaro Arbeloa

Manchester United crumbled with only 10 men on the field and the Spanish giants claimed a huge european scalp to progress through to the next round.

It was a roller coaster of a night for Nani, who in most people's opinion was harshly punished for a fairly innocuous challenge.

Take a look below at the pictures and share in the agony and the ecstasy of a night in Nani's boots

Photo gallery Nani's night in pictures See Gallery
Photo gallery Manchester United Vs Real Madrid See Gallery