George Best: Played in games against Real Madrid during his Manchester United career

Whether it be UEFA Champions League and Cup Winners' Cup finals, group stage classics or thrillers from throughout the years of European competition, Manchester United have a long history of memorable meetings with Spanish clubs.

But, although there are highlights, England's most successful league club possess a surprisingly poor record against opponents from Spain having recorded a win percentage of just 24% from 45 games and conceded a negative goal difference.

Under-pressure United manager David Moyes, who inherited that record this summer from his predecessors, will be desperate to address those statistics when taking on Real Sociedad at Old Trafford in this season's Champions League Group A on Wednesday.

But history does not bode well ahead of the Matchday Three contest, with United having won just one of their last six games at Old Trafford against La Liga clubs. Here, we remember a mixture of United's best and worst moments against Spanish opposition over the decades.

Man United v Spanish Clubs Played Wins Draws Losses Goal Difference 45 11 18 16 -9

Man United 3 Athletic Bilbao 0 (Agg: 6-5) - European Cup quarter-final - 1957

Having lost the first leg 5-3 in Spain, Sir Matt Busby's Busby Babes produced a thrilling comeback at Old Trafford in the second leg. Dennis Viollet scored before half-time to give United some hope. Then, in the 70th minute, Tommy Taylor brought the sides level on aggregate and, in the 85th minute, Johnny Berry completed an epic turnaround. Busby's side then lost in the semi-final in a 5-3 aggregate defeat by Real Madrid.

Real Madrid 3 Man United 3 (Agg: 3-4) - European Cup semi-final - 1968

Despite taking a 1-0 first-leg lead from George Best's goal at Old Trafford, Busby's United seemed to be on their way out as the second leg at the Bernabeu entered its final 17 minutes. Real were ahead 3-1 on the night and 3-2 in the tie. But David Sadler stunned Real when he pounced on Best's free-kick before Munich air disaster survivor Bill Foulkes scored the most important goal of his career to send United through. United then beat Benfica in the final.

Man United 2 Barcelona 1 - Cup Winners' Cup final - 1991

United claimed European glory in this final in Rotterdam when Mark Hughes proved to be the hero against his former club, Barcelona. Hughes opened the scoring with a tap-in in the 67th minute and then doubled United's lead with just more than a quarter-of-an-hour remaining. A trademark Ronald Koeman free-kick gave Barcelona a lifeline but Sir Alex Ferguson's United were able to hold on and lift the trophy.

Atletico Madrid 3 Man United 0 (Agg: 4-1) - Cup Winners' Cup second round - 1991

United's defence of the Cup Winners' Cup came to a swift end when they were eliminated by Atletico Madrid in the following season. A 3-0 defeat in the first leg in Madrid, where Portugal international and future West Ham United player Paulo Futre scored twice before Atletico legend Manolo added a third, proved too much to overcome. A 1-1 draw in the second leg at Old Trafford was consequently far from enough to save United.

Barcelona 4 Man United 0 - Champions League group stages - 1994

Johan Cruyff's Barcelona claimed comprehensive revenge over United for their Cup Winners' Cup final defeat of a few years previous in what was a lesson for Ferguson's men in their early years in the Champions League. A team featuring the likes of Pep Guardiola were comfortable winners at Camp Nou thanks to two goals from Hristo Stoichkov either side of one from Romario before Albert Ferrer completed the rout.

Barcelona 3 Man United 3 - Champions League group stages - 1998

United would famously go on to win the Champions League this season in the most dramatic fashion but their meetings with familiar foes Barcelona in the group stages were not without excitement. Having already drawn 3-3 at Old Trafford, the two teams repeated that scoreline at Camp Nou, where dynamic strike duo Dwight Yorke (twice) and Andy Cole were both on target for the visitors.

Man United 2 Real Madrid 3 (Agg: 2-3) - Champions League quarter-finals - 2000

After a goalless first leg at the Bernabeu, defending champions United were in confident mood ahead of their decider with Real at Old Trafford. But those hopes were soon dashed as the visitors raced into a three-goal lead through a Roy Keane own goal and two goals from Raul. That rendered late efforts from David Beckham and Paul Scholes meaningless as they were dumped out.

Man United 4 Real Madrid 3 (Agg: 5-6) - Champions League quarter-finals - 2003

After losing the first-leg 3-1, Ferguson dropped a bombshell by leaving out Beckham for the second leg at Old Trafford. It did not work on any level for the United boss. Three times Real led, with Brazil international Ronaldo famously scoring a wonderful hat-trick before leaving to a standing ovation. Beckham's introduction triggered a comeback of sorts but the England man's brace just left Ferguson with even more egg on his face.

Barcelona 3 Man United 1 - Champions League final - 2011

Having two years earlier been well beaten by Barcelona in the Champions League final in Rome, United were out to set the record straight at Wembley. However, Barcelona, then managed by Guardiola and considered by many to be the best club side in history, produced a mesmerising masterclass. Wayne Rooney's goal was rendered meaningless by Pedro, Lionel Messi and David Villa, which left Ferguson to say: "No-one has given us a hiding like that."

Man United 1 Real Madrid 2 (Agg: 2-3) - Champions League quarter-finals - 2013

A devastated Ferguson could not bring himself to face the media after United's second leg defeat by Jose Mourinho's Real at Old Trafford last season. He had not made it known publicly at the time but the Scot knew it was his last try at winning a third European Cup before he retired. To make matters worse, former United superstar Cristiano Ronaldo was among Real's goalscorers in both legs.

You can watch Manchester United v Real Sociedad live on Sky Sports 2HD and 3D on Wednesday from 7.30pm