The 7 Most Heartbreaking Moments in Chelsea History

Every fan supporting their clubs have had their moments of joy and pride for supporting the team. The joy of being a supporter of a title winning club is unparalleled. But life isn't a bed of roses, and each club will have gone through heartbreaks that would have brought a tear to every fan. 

Chelsea FC, a club that only after Roman Abramovich's takeover started to win titles on a regular basis, have not escaped the agony of a heartbreak.

Lets take a look at seven of those moments that would have driven a spear through the heart of every Chelsea fan.

Bye Bye Jose Mourinho

Jose Mourinho,the self proclaimed "Special One" was brought to Chelsea for one reason—to win titles.

He did precisely that by delivering two Premier League titles, one FA Cup, one Community Shield and two League Cups. To add to this list of success stories were two semi-final appearances in the Champions League—and both of those journeys ended at Anfield. 

When the 2007-08 season started the expectation was that Chelsea would mount another challenge on the Champions League, but the months preceding the start of the new season were marred by conflicts between Roman and Jose regarding team selection and player transfers.

Chelsea's season got off to the usual start by winning their first 3-4 games. The wheels started to come off after a defeat to Aston Villa followed by tame draws to Blackburn in the Premier League and Rosenborg in the Champions League . Following this was the body blow to Chelsea FC—Jose Mourinho resigned as manager by "mutual consent".

His successor Avram Grant never really got the respect from the Chelsea faithful as they, like the Chelsea squad, were staunch Mourinho supporters. Chelsea never really attained managerial stability ever since the Special One departed the shores of Stamford Bridge, as many a top manager like Luiz Felipe Scolari and Carlo Ancellotti failed to emulate what Mourinho had achieved at the Bridge

The 'Slip' of the Champions League from Chelsea's Hands

The 2008 Champions League final at Moscow was a clash of the two heavyweights of the Premier League; Manchester United and Chelsea.

Manchester United had just won the Premier League title after a close race with a Chelsea side that had made vast strides after the departure of Jose Mourinho at the start of the season. 

It was a game that brought fans to the edge of their seats as both teams came into this game with a good run of form behind them and fully fit squads.

It was United who took an early lead through Cristiano Ronaldo who had been in tremendous form in the season. United dominated proceedings until a tactical change by Avram Grant brought Michael Essien from a right full back position to the centre of midfield. That move saw a sudden surge of Chelsea attacks, that culminated in an unusual equaliser from Frank Lampard.

Both teams went into the break at level pegging. 

The second half saw both sides creating numerous chances, and this continued into both halves of extra time during which Didier Drogba lost his head and slapped Nemanja Vidic right in front of the referee. Fate had decided that both teams were too good for the match to be decided on regulation time, and penalties it was.

It was all square even during the penalty shootout until Cech pulled off a miraculous save from Ronaldo's shot to leave John Terry to create history by one simple kick of the football. It was not to be his day, however, as the Chelsea captain slipped while taking his penalty and the ball struck the upright.

JT was distraught as they were back to square one. Giggs converted the next penalty and Salomon Kalou followed suit. Then Van der Sar pulled off a brilliant one-handed save to deny Anelka, and United were champions for a third time. 

It left the Chelsea fans gutted, and wondering had Drogba not been sent off it would have been him that would have taken John Terry's penalty, and they would probably be singing all the way back to London.

It has left an inedible mark on Chelsea as the memories of Moscow surface every time they faced United in a Champions League clash

The Ghost of Anfield

Jose Mourinho looked set for second successive Champions League final appearances, as his Chelsea side travelled to Anfield for the second leg of their Champions League semi final with both sides on a goalless stalemate.

Chelsea needed to keep their cool in a ground where European nights shattered decibel levels, and hostility was part of the game. 

Both sides started the game tentatively, but Liverpool gradually took hold of the game through their quick passing and movement, but they were up against a very stingy Chelsea defence.

It took one quick move to create a chance as Luis Garcia played a one-two with Steven Gerrard who chipped it over the Chelsea back line as Garcia got the slightest of touches to beat the advancing Petr Cech.

As the world watched the ball bouncing towards the goal, William Gallas rushed to smack the ball out of play just when the ball was about to cross the line. Fans were celebrating as the assistant referee had awarded the goal amidst protests from the Chelsea players that the ball hadn't crossed the line. 

Chelsea never really recovered from that early goal as they looked shady and out of sorts. Arjen Robben, who had just recovered from an injury, came on to introduce some flair into the Chelsea side, and he almost equalised as he side-stepped two Liverpool defenders but blasted his shot above the bar.

Gudjohnsen had probably the best chance as he volleyed wide with the goal at his mercy. Liverpool won the game and went on to win the Champions League in a historic final against AC Milan. 

Chelsea fans would have felt gutted by the decision of the assistant referee. Two seasons later it was a chance at redemption for Chelsea as they faced Liverpool again in the semi finals. The scenario was different as Chelsea arrived at Anfield with a 1-0 lead, though it was quickly cancelled out by Daniel Agger's early goal. Chelsea went on to lose in penalties, and they would have to wait for a little longer before they got one over Liverpool.

Last but Not the Least: Iniesta's Goal to Seal His Place Amongst the Barca Elite

It was another Champions League season that involved a managerial merry go round at Chelsea. Avram Grant was unfairly sacked after the heartbreak of Moscow, to be replaced by 2002 World Cup winning coach Luiz Felipe Scolari.

Scolari did not last long as he was replaced by Guus Hiddink, Abramovich's close friend and then manager of a Russian football team that turned some heads during Euro 2008. Chelsea showed remarkable progress and stability all the way to the Champions League semi-final, where they would face old rivals Barcelona, managed by a new manager in Pep Guardiola.

The first leg at the Nou Camp was a case of Chelsea occupying their own half for the whole 90 minutes to come away with a clean sheet, becoming the first team to stop Barca from scoring. 

Chelsea needed to win in the second leg, and confidence was high after the high octane clash with Liverpool in the quarter finals. Chelsea got off to the perfect start with Micheal Essien's brilliant left foot volley from the edge of the box. Then Chelsea broke down Barcelona's fluid Tiki Taka passing game and never gave them an inch.

The game was marred by many penalty claims by Chelsea. Abidal's fouls on Malouda and Drogba inside the penalty box, if given, would have surely put the game out of Barcelona's reach.

It wasn't to be.

Chelsea were already celebrating when their joy turned to utter sorrow, when Andres Iniesta got on the end of a pass and struck a beautiful volley with the outside of his right foot to latch itself onto the top corner of the Chelsea net.

Stunned silence was what followed, in addition to Ballack throwing himself onto the face of the Norwegian referee to claim handball—and Drogba's rant to the television cameras after the game. 

It would have meant a shot at redemption for Chelsea had Iniesta not scored. This was a match that exemplified the saying ' its not over until the fat lady sings'

"I Have Not Been Beaten at Stamford Bridge and Never Will Be": The Special One

It was the most anticipated match of the 2009-10 Champions League. Carlo Ancellotti had managed to make an ageing Chelsea squad into a cohesive, tight unit who were dominant in the Premier League.

Likewise for Inter, Mourinho had learnt from his mistakes during the previous season, and they were again on course for another Scudetto.

It was a high voltage clash for two reasons. Firstly, it reignited the Ancellotti-Mourinho rivalry which was prominent when Carlo was in charge at Milan. Secondly, it marked the return of the Special One to his former stomping ground. He was determined to prove to Roman what a mistake he had made by letting him go. 

Chelsea held an advantage having come away from the San Siro with an all important away goal. With the exception of the goalkeeper, Chelsea had a fully fit squad. Jose on the other hand was expected to field a side that would park the bus and prevent Chelsea from scoring. Jose threw everyone a surprise by naming a highly attacking lineup to go for the win. 

Chelsea created numerous chances but failed to capitalise. It took just one brilliant move by Inter to put Samuel Eto'o clear of the Chelsea defence and put it past Chelsea keeper Ross Turnbull. After that, Chelsea were shell shocked and never looked like wanting to get back into the game, Drogba's late sending off capped off a miserable night for the Blues

Ancellotti may have had Chelsea running on all cylinders in the league, but in the Champions League, and more importantly at Stamford Bridge, it was seen that The Special One ruled the roost

Barcelona: The Bane of Chelsea in the Champions League

Lets take a short trip down memory lane. One that Barca fans will love to remember and one that Chelsea fans will want to forget.

The Blues, under Gianluca Vialli, named an attacking lineup to counter a Barcelona side oozing with class. After some adjusting to the game by both the teams, Chelsea got on the scoresheet through Torre Andre Flo's free kick, to give some much needed confidence. It was to turn into disbelief for both sets of fans as Flo doubled Chelsea's lead by tapping in Zola's pass. 

It turned to ecstacy when Flo got a hattrick four minutes later, and Chelsea went into halftime with a huge advantage. Barcelona had been hit, and hit badly. 

Chelsea continued the tempo during the second half, though Figo got the vital away goal after latching onto Cocu's return ball. It was advantage Chelsea for the second leg.

It's always a daunting task to play Barca in the Nou Camp. Chelsea came with a defensive mindset hoping to shut Barca out completely. Barca began to impose themselves onto the game against a rather defensive Chelsea midfield.

24 mins into the game and Barca got the goal they wanted. Rivaldo's free kick deflected off Babayaro and into the Chelsea net. At the stroke of halftime Chelsea were down 2-0 thanks to Kluivert's shot, that crashed against the bar onto the feet of a gleeful Figo to pass the ball into the net. 

Some stern words would have been spoken during half time as Chelsea hit back after a disaster in the Barca defence, allowing Flo to pull one back and putting Chelsea back in the driving seat. Dani swung the game towards extra time, as his deflected effort put Barcelona at 3-1. Extra time and penalties loomed.

Into extra time, Figo ran rings around the Chelsea defence before being brought down by Babayaro, who was then sent off. Rivaldo, who missed an earlier penalty, was as cool as ever and slotted it past de Goey.

Down to 10 men and losing the game, Chelsea switched off and allowed Kluivert to latch onto Dani's cross and finishing the game for Barcelona, and ending Chelsea's European dreams.

Goodbye Claude: We Will Never Forget You

His ability to bring teams out of the mud is what that makes him a renowned coach. Claudio Ranieri helped Cagliari earn successive promotions, helped Napoli to a fourth place finish in Serie A and also achieved promotion to Serie A with Fiorentina before moving to Valencia.

Here he brought about changes that would make them a fighting and impressive team, in the form of Gaizka Mendieta, Angulo and Santiago Canizares. He helped them qualify for the Champions League and also brought the Copa del Rey to Valencia. 

Such feats attracted the attention of Chelsea who needed someone to reduce the average age of the squad, and bring a fresh approach to Chelsea. After some initial hiccups with regards to the language barrier, Ranieri managed to guide Chelsea to a UEFA Cup spot. 

He was busy during the following transfer window by signing young and quality international players in the form of an emerging Frank Lampard from West Ham, Emmanuel Petit and Zenden from Barcelona, Jesper Gronkjaer from Ajax and William Gallas from Marseille and selling Dennis Wise, the Chelsea favourite. Despite these changes, Chelsea disappointed as they lost to Arsenal 2-0 in the FA Cup final.

He was responsible for allowing talents like John Terry, Robert Huth and Carlton Cole to develop and managed to get the best out of the underperforming players at the club.

The 2003-04 season was known more for Roman Abramovich's takeover at Chelsea, and it gave Ranieri license to spend freely. He brought in Damien Duff, Wayne Bridge, Glen Johnson, Adrian Mutu, Juan Sebastian Veron and Hernan Crespo to form a formidable squad.

This was to be another season that ended on a low note, as Chelsea lost to Monaco in the Champions League semi-final amid constant rumours that Sven Goran Eriksson would be replacing Claudio.

Rumours that Ranieri would be sacked became commonplace, but he brought a few finishing touches to the club by leading them to a 2nd placed finish in the Premier League and signing Petr Cech from Rennes and Arjen Robben from PSV. 

Much as anyone would say that the current Chelsea team was built by Mourinho, it was Ranieri who was the true architect of forming the spine of a Chelsea team that would serve them very well in the years to come