Manchester United have missed out on the last-16 of the UEFA Champions League for the first time in six seasons after losing 2-1 to Basel at St. Jakob-Park.
Alexander Frei was the match-winner with an 85th minute header after Marco Streller gave the home side a ninth-minute lead, although Phil Jones did net an injury-time consolation.
The Red Devils made the brighter start to the contest, but fell behind when Marco Streller converted Xherdan Shaqiri's drilled left-wing cross at the back post.
The visitors were down to ten men when the ball found the back of David De Gea's net as Chris Smalling
was down after being caught by Nemanja Vidic's elbow attempting to clear the danger.
was down after being caught by Nemanja Vidic's elbow attempting to clear the danger.
Wayne Rooney missed a gult-edged with 30 minutes played when he mis-hit Nani's teasing right-wing cross from close range while Park ji-sung saw his follow-up smothered by Basel goalkeeper Yann Sommer.
Rooney could only find Sommer from Ryan Giggs' inside ball and they suffered a blow before half-time when defender Vidic was stretchered off with a knee injury.
The visitors came within a whisker of equalising after the interval when right-back Markus Steinhoefer diverted Nani's cross onto the underside of his own crossbar leaving Sommer rooted to the spot.
United hopes of progressing were dealt a devastating blow in the closing stages when Frei converted Shaqiri's cross, although the visitors did manage to pull one back from Jones' header.
On the other side of town Manchester City defeated Bayern Munich 2-0 at the Etihad Stadium, but they were made to pay for mistakes earlier in their European campaign as they were eliminated from the UEFA Champions League.
Roberto Mancini's squad went into Matchday Six with the odds stacked against them and, although they defeated the Bundesliga leaders,Napoli's win at Villarreal condemned them to Europa League football in 2012.
David Silva's wonderful opener and Yaya Toure's second ensured City finished with a win, but they had to regret an away defeat to Bayern and a failure to beat Napoli at home before losing in Italy.
