UEFA Champions League: 15 Biggest Blunders in UCL History

The UEFA Champions League is European soccer's grandest stage.

The epic battles fought in this tournament are forever recorded in the annals of club football history.

Some of the greatest players have had their greatest performances in the tournament, but the beautiful game often causes more pain than pleasure.

For every great Champions League performance, there is also a terrible one.

Here are the 15 most memorable gaffes in Champions League history.

15. Manchester United Knocked out Early by Basel

Manchester United started its 2011-12 Champions League campaign in search of a fifth finals appearance in four years. But United's tournament came to a shockingly early end in December after a 2-1 defeat at the hands of FC Basel.

The Red Devils received a supposedly easy draw in the group stage, with Basel and Benfica not expected to pose a serious threat.

Both teams caused massive problems for United, and the reigning runners-up went 0-1-3 in four games against the two teams.

On December 7, 2011, United only needed a draw to go through to the knockout stages, and no one expected Basel to stand in its way.

In just the ninth minute of the game, Marco Streller's volley put the Swiss team ahead. The English side scrambled to find an equalizer, but Alexander Frei's header in the 84th minute sealed Basel's advancement.

United is now left to shamefully compete in the Europa League.

14. Manchester City Fails to Make It Through to Knockout Stage

Manchester City faced much tougher competition than their crosstown rivals in the group stage of the 2011-12 Champions League tournament, but with the amount of money spent to assemble the current squad, there is no excuse for City's failure to advance.

The team was lumped in with German powerhouse Bayern Munich and an energetic Napoli team, and they struggled the whole way through.

All three clubs easily dealt with Villarreal, the group's fourth member, but City dropped matches to both Bayern and Napoli.

In the final game of the group stage, the current EPL leaders performed at the level they needed to and dispatched with Bayern 2-0. 

Unfortunately, City's shoddy play in the earlier games put their fate in the hands of Napoli. The Italian side defeated Villarreal 2-0 to finish one point ahead of the Blues, who became the second Manchester side to be eliminated that day.

13. Manchester United Exits Early After Loss to Benfica

The 2011-12 Champions League draw likely brought up painful memories for Manchester United, considering that Benfica and Villarreal were both in the team's group last time it failed to advance to the knockout round in 2005-06.

The similarities between United's dismal showing this year and their poor play in 2005-06 do not end there. On December 7, 2011, United was defeated 2-1 by Basel and eliminated from the Champions League. On December 7, 2005, United was defeated 2-1 by Benfica and eliminated from the tournament.

The loss capped off a disappointing stretch of play by the Red Devils, who earned just one win in the group stage and finished tied with Lille for last in the group.

Hopefully, for United supporters, next year's draw for the group stages will keep the team away from Benfica and Villarreal.

12. Celtic Loses 5-0 to Artmedia Bratislava

Roy Keane helped Celtic FC to a Scottish Premiership title in his only season with the Glasgow-based club, but was also part of one of the most embarrassing losses in the team's history.

Celtic was no stranger to the group stage of the Champions League, but rarely advanced past it. For smaller clubs in smaller leagues, reaching that point in the tournament is extremely lucrative, earning a team around £10 million. 

In the 2005-06 tournament, Celtic hit a major obstacle en route to another payday when they faced Slovakian champions Artmedia Bratislava (now named FC Petržalka). 

The first leg of the matchup became the story of the summer, when the Slovaks defeated Celtic 5-0. 

When asked about the game, Celtic manager Gordon Strachan said, "I have been manager for eight years and a player for 25 years and this is out-and-out the worst football night I have ever had."

Celtic managed to avenge the embarrassing defeat, beating Artmedia Bratislava 4-0 in the next leg, but the Slovakian team still won 5-4 on aggregate and advanced into the group stages.

It was a magnificent accomplishment for the underdogs, considering their entire annual budget was just £1 million.

11. Rafael's Red Card Against Bayern Munich

The 2009-10 Champions League clash between Manchester United and Bayern Munich was one of the most exciting and controversial quarterfinals the tournament has seen.

Bayern took the first leg 2-1, but in the second game, United came out firing and went up 3-0 in the first half. Bayern struck back just before halftime and faced a 3-1 deficit at the break.

The game changed very quickly in the second half. After going forward, United defender Rafael da Silva chased down Franck Ribery, who went to the ground all too easily when the young Brazilian caught up with him.

After the play, the referee was immediately surrounded by hysterical Bayern players shouting for Rafael to be carded. The official caved to the pressure and awarded a second yellow card, taking United down to 10 men.

In the first half, the Red Devils' other outside back, Patrice Evra, had completely nullified the presence of Bayern winger Arjen Robben.

Once United was missing a defender, Robben found space and was able to abuse the slower center backs, who were forced to guard the Dutchman while playing shorthanded.

Robben steadily built up confidence, and scored an incredible goal on a volley off of a corner kick. United won the game 3-2, but Bayern advanced on away goals.

The quarterfinal matchup was essentially the semifinals, as Bayern would play the winner of Bordeaux and Lyon, two weaker French teams. The German side would defeat Lyon 4-0 on aggregate en route to one of the most boring Champions League finals in recent years. 

10. Robin Van Persie's Red Card Against Barcelona

Barcelona went on to win the 2010-11 Champions League Final, but they were helped out by referee Massimo Busacca in a matchup in the first knockout stage with Arsenal.

The Gunners defeated Barça 2-1 in the first leg and were playing excellent football in the second match with the score tied at 1-1 in the second half.

A harmless offside call on Robin van Persie changed the whole game when Busacca decided that the Dutch striker was attempting to waste time by kicking the ball just one second after the whistle blew.

Van Persie was given his second yellow card of the game and was livid at the referee's decision. Without their best striker, the Gunners could not hold off the Barça attack.

The Spanish champions scored two more goals and went on to dominate the rest of the tournament and bring home a trophy.

9. Carlo Ancelotti Plays Fernando Torres in Favor of Didier Drogba

During the January transfer window in 2011, Chelsea once again made the biggest headlines by spending £50 million on Fernando Torres; unfortunately, the Spaniard has not lived up to expectations at Stamford Bridge.

In the 2010-11 Champions League quarterfinal Chelsea was matched up with rival Manchester United and immediately made things difficult for themselves by losing the first leg 1-0 at home.

Needing a victory, manager Carlo Ancelotti inexplicably sat Didier Drogba in favor of Torres, who had been in awful form.

El Niño looked lost and confused for the entire first half. When Chicharito Hernandez gave United a 1-0 lead just minutes before the break, Ancelotti had seen enough.

The Blues boss pulled Torres at halftime and gave Drogba the opportunity he had deserved 45 minutes earlier.

The long-time Chelsea striker would go on to tie the game at 1-1, but Ji-Sung Park broke the tie just seconds later, giving United a 2-1 victory and a trip to the semifinals.

8. Real Madrid's Six Consecutive First Knockout Stage Exits

Real Madrid made it all the way to the semifinals of last year's Champions League tournament, but before that, the Galácticos were bounced out of competition in the first knockout stage in six consecutive years.

The streak started when Madrid was beat 2-1 on aggregate by Juventus in 2004-05, and the low point came in 2008-09 when Liverpool beat them 4-0 at Anfield to win the round 5-0 on aggregate.

The next season, management cleaned house and spent €224 million (about $293 million) in transfer fees on Cristiano Ronaldo, Kaká, Xabi Alonso and Karim Benzema.

With a new set of superstars, Madrid came into the Champions League with renewed hope, but were stunned by Lyon and lost in the first knockout stage 2-1 on aggregate.

This completed the six-year streak of underachievement that will forever haunt Madrid fans.

7. Phantom Hand Ball Keeps Barca from Moving on

In the 2009-10 Champions League semifinal, Barcelona was looking to become the first team to win the tournament (in its current format) two consecutive times.

The Spanish side faced an intriguing matchup with Inter Milan, with whom they had swapped center forwards with in the offseason. Zlatan Ibrahimovic and Samuel Eto'o each had an opportunity to prove their worth to their old clubs.

Barcelona showed poor defense of its title in the first leg and lost 3-1 at the Camp Nou.

When the two teams played at the San Siro, Inter manager Jose Mourinho had La Blaugrana exactly where he wanted them.

Mourinho was infamous for protecting leads, and the Italian side hunkered down in the back and went for a 0-0 tie.

The game was scoreless until the 84th when Gerard Pique brought Barça one goal away from the finals with a brilliant move and finish in the box.

The drama meter was pushed into the red when Bojan Krkic appeared to put Barcelona through, but the goal was called back because of an alleged handball by Yaya Toure.

The questionable decision ended Barça's title defense, and the game's official will forever be a villain in Catalonia. 

6. Juventus Allows Manchester United to Come Back from 2 Goals Down

Before Manchester United's historic comeback against Bayern Munich in the 1998-99 Champions League Final, the team had to stage a historic comeback against Juventus in the semifinal.

The two teams tied 1-1 in the first leg at Old Trafford, and United headed to Turin hoping to become the first English side to reach the tournament's final.

Disaster struck early in the form of Pippo Inzaghi, who scored twice in the first 11 minutes of the game. 

With doubt starting to drown United, Roy Keane showed why he would be the man to take over the captaincy from goalkeeper Peter Schmeichel after the Dane's impending retirement.

Keane had already been issued a yellow card and would miss the final, but put away a fantastic header to cut Juve's lead in half.

The goal would spark two more unanswered strikes from United as Juventus tried helplessly to hang on to its seemingly insurmountable early lead.

5. Jens Lehmann's Red Card in Champions League Final

The 2005-06 Champions League final looked to be an entertaining matchup with superstars like Thierry Henry and Ronaldinho on the field, but it was Jens Lehmann who made the most decisive play of the match.

Arsenal looked to have the clear advantage at the start, with Henry narrowly missing two quality opportunities in just the first few minutes. 

The Gunners were unable to capitalize when they had early momentum, and in the 18th minute Jens Lehmann stopped a Samuel Eto'o breakaway by sliding in like a madman and upending the striker. Lehmann was sent off and Arsenal was forced to play shorthanded for the rest of the match.

The English side was able to settle into a defensive style of play and unleash an occasional counter attack. Barcelona would go on to dominate possession for the rest of the match.

Despite Barça's advantage, Arsenal was able to strike first when Sol Campbell headed home an Henry free kick in the 37th minute.

In the second half, Barcelona continued to build pressure and seemed destined to score. Arsenal was able to create a few chances on breaks up the field, but the defense could not hold off their opponent's potent attack.

The Spanish club used their one-man advantage and scored two goals in the final 14 minutes to take home the trophy.

4. AC Milan Loses 4-0 to Deportivo La Coruña in Quarterfinals

In the early part of the 2000's, AC Milan was at the height of its power and proved it with a 4-1 thrashing of Deportivo La Coruña in the first leg of the Champions League quarterfinals.

In the second leg, Milan suffered one of the most shocking losses in world football history. 

Playing in Spain, Deportivo netted its first goal in just the fifth minute, and Milan's monumental collapse began. 

The Spanish side took a 3-0 lead into halftime and came out just as strong after the break.

Deportivo struck once more in the second period and erased the memory of the first-leg loss by winning the round 5-4 on aggregate.

Unfortunately for Milan, this would not be the only time they suffered a monumental collapse in the Champions League.

3. John Terry Misses PK in Champions League Final

In their book Soccernomics, Simon Kuper and Stefan Szymanski give an intriguing account of the penalty kick shootout between Manchester United and Chelsea in the 2007-08 Champions League final.

Chelsea manager Avram Grant prepared for the possibility of a penalty shootout by hiring an economist to analyze the tendencies of the United kick-takers and of goalkeeper Edwin van der Sar. 

The economist's research showed a recurring pattern in Cristiano Ronaldo's habits: The winger would wait until the last second to decide which direction to shoot, hoping the keeper would tip his hand as to where he was diving. If the keeper gave away no hints, Ronaldo would shoot to his left. 

As for van der Sar, he would almost always dive to a player's "natural side." A right-footed player shooting to his natural side would shoot left, and vice versa for lefties.

In the shootout, Chelsea keeper Peter Cech stood still as a statue as Ronaldo stutter-stepped towards the ball, then dove to Ronaldo's natural side and blocked the shot.

When it was the Blues' turn to shoot, every player shot high and away from their natural side, and they all converted, until it was captain John Terry's turn.

Nothing in the economist's research accounted for the possibility of human error, and it was colossal error that doomed Chelsea. Terry was aiming high and away from his natural side, but slipped as he struck the ball and clanged the shot off the post. 

As the game went into extra kicks, van der Sar figured out Chelsea's strategy and intimidated Nicolas Anelka by pointing to the direction in which all of the shots had been taken. Anelka proceeded to shoot to his natural side and the Dutchman denied him, giving United the trophy.

2. Bayern Munich Allows Two Stoppage-Time Goals in Final

Manchester United had already won the English Premier League and the FA Cup by the time they faced Bayern Munich in the 1998-99 Champions League final. 

This United team developed a habit during the season of never making things easy on themselves, and the matchup with Bayern was no different.

The Red Devils were without world-class central midfielders Roy Keane and Paul Scholes. Both players had a penchant for thuggery and had accumulated too many yellow cards in the earlier knockout stages.

To make matter worse, United defender Ronny Johnsen committed a silly foul at the top of his own box in the sixth minute, and Bayern striker Mario Basler promptly bent the ball around the wall and into the net.

The English side would trail for nearly the entire game, but the team had one last surprise for the football world.

Teddy Sheringham and Ole Gunnar Solskjaer were brought into the game to generate offense, and each player scored in stoppage time to give United a 2-1 victory in the most dramatic fashion possible.

The goals completed the Treble and a legendary season for the Red Devils.

1. AC Milan Blows Three-Goal Lead to Liverpool

On European football's grandest stage, AC Milan displayed the greatest collapse in European football's history.

Milan was hoping to avenge a shocking loss to Deportivo La Coruña in the previous year's Champions League when they faced Liverpool in the 2004-05 tournament finals.

The Italian team's talisman, Paolo Maldini, set the pace for his team by opening the scoring in very first minute. 

Milan would double its lead on a Hernán Crespo goal in the 39th minute. In the 44th minute, Kaká unleashed a deadly pass that sliced through the Liverpool defense and gently landed at Crespo's feet. The Argentinian made quick work of the finish to give his team a 3-0 lead at halftime. 

In the second half, Liverpool took off Steven Gerrard and brought on Superman. Hyperbole aside, Gerrard was possessed in the second half and dominated the center of the field. 

The Liverpool captain scored his team's first goal on a fantastic header in the 54th minute. Just two minutes later, Vladimír Šmicer fired a shot across the goal and into the corner to make the score 3-2.

Liverpool continued to furiously attack and in the 60th minute; a piercing run from Gerrard led to penalty kick that Xabi Alonso converted to complete the comeback.

Regulation time ended with the score at 3-3, and after two overtimes the game went into shootouts. Liverpool had come too far to lose, and goalkeeper Jerzy Dudek denied Andriy Shevchenko to give his team the trophy. 

Dudek's save also ensured that Milan's performance would be remembered as the greatest blunder in UEFA Champions League history.