Chelsea FC: Most Successful Seasons in Blues History

Chelsea Football Club was founded in 1905, and are one of few clubs that were founded specifically to fill the void of a venue, in their case, Stamford Bridge.

Although the current era has been the most successful for the club by far, there are still great years in the past, and great managers and players that have brought the club to where it is today.

With many seasons on par as extremely important to the overall history of the club, the Blues have a unique chronology that literally sees the club progressing over time much more than digressing, as we take a look at the most successful seasons in Blues history.

1954-55 First League Title

Chelsea took 50 years to win their first English first division title. Strong leadership by Englishman Ted Drake of the then-nicknamed "Pensioners" saw the club rise to the occasion.

The club managed to wrestle away the top spot from a tough Wolverhampton Wanderers club that were in the height of their power during the mid-to-late 1950's.

Chelsea's victory not only saw them lift their first English title or trophy of any kind, their title saw them become the inaugural English club to enter the European Cup, which would become the UEFA Champions League. However, Chelsea chose not to participate in the tournament.

A victory in the FA Community Shield would also come at the start of the following season as 1955 would see not one, but two first trophies for the club.

1964-65 First League Cup Title

Chelsea took a nose dive out of the league when they were relegated in 1961-62. A two year stint in the second division saw them return to the top flight and finish fifth in 1963-64. Chelsea went into the 1964-65 season once again pushing for glory.

Their change came in the League Cup that season and they would eventually defeat the defending champions, Leicester City, 3-2 on aggregate, becoming the first London based club to win the competition and denying the Foxes a repeat.

1969-70 First FA Cup

Chelsea won their first FA Cup title in the 99th edition of the world's oldest association football tournament. The Blues won their title in dramatic fashion by battling the mighty Leeds United of Don Revie to a 2-2 draw at Wembley in their first match to force a replay.

The clubs were level at 1-1 before Leeds forward Mick Jones scored the go-ahead goal at the 84th minute. However, the Blues refused to go quietly, as only two minutes later an 86th minute equalizer from Ian Hutchinson brought the clubs level once more.

In the second match to decide the victors, the two clubs met at Old Trafford, the famous ground of Manchester United. Mick Jones struck once more for Leeds, putting them up early. Chelsea again refused to go away, as an 78th minute goal from Peter Osgood would see the two go to extra time where defender David Webb would put the Blues on top in the 104th minute and see them close out a 2-1 victory in epic fashion.

1970-71 First European Silverware

Chelsea rode the back of their previous FA Cup success into the UEFA Cup Winner's Cup, that saw Europe's domestic Cup elites drawn together.

The Blues dominated their way to the final where they would face off against European competition's darling club, Real Madrid.

Once again the London club would force a replay in a cup final only to win 2-1 in their replay, thanks to two goals in six minutes from Peter Osgood and John Dempsey, and lift their first piece of European silverware.

1996-97 Return to FA Cup Glory

Chelsea would endure a torrid period from the mid 1970's through the early 1990's that would see them relegated not once, but twice, and be forced to fight their way back to the first division on two separate occasions.

However, the arrival of legendary Dutchman Ruud Gullit to the Chelsea managerial hot-seat saw the club finally find their way back to FA Cup glory, and helped spark the current golden era of Blues football. Gullit was the first non-British manager of the club, and would start the trend of foreign leaders in the Blues' managerial spot.

The Blues would not need a second chance for this final, as an opening minute goal from Roberto Di Matteo stunned Middlesbrough and an 83rd minute strike from Eddie Newton would seal the victory, earning the club their first trophy in 26 years.

1997-98 First Two Trophy Season

Chelsea would secure two trophies for the first time during the 1997-98 season under the leadership of manager Gianluca Vialli.

The Blues would lift two trophies between March and May of 1998 as the first came with a 2-0 victory to seal the League Cup over Middlesbrough in a rematch of the 1996-97 FA Cup final.

Victory in the League Cup would lead the club to battle their way to the UEFA Cup Winner's Cup final for the second time in their history, and a single goal from Gianfranco Zola would be all they needed to claim a 1-0 victory over VfB Stuttgart.

2004-05: The First Taste of Jose Mourinho

Chelsea's new owner Roman Abramovich wasted no time in chasing down the best of the best when he hired promising managerial candidate Jose Mourinho from FC Porto after having led the Portuguese giants to two straight league titles, a UEFA Cup and a UEFA Champions League title.

His first season in London saw him embrace the club and the fans, as they did the same, while the players worked their socks off to win both the League Cup and their first ever English Premier League—their first top flight title in fifty years.

2005-06: Nothing Like a Repeat

Not only were the Blues hungry for more success in 2005-06, but they were bound and determined to dominate the league as they had in the previous season, and they opened the campaign with an FA Community Shield triumph.

Jose Mourinho would accept nothing less than more results as once again they won the EPL title by a convincing margin. It was the first and only time the club's history to win back to back titles in any competition.

2006-07: Domestic Cup Double

Although the most highly sought after domestic double in England is the pairing of the English Premier League title with an FA Cup trophy, Jose Mourinho would manage once more to take two pieces of silverware back to Stamford Bridge.

The first came with a League Cup final victory over Arsenal, thanks to a Didier Drogba brace after young Theo Walcott had put the Gunners on top at the 12th minute. 

Chelsea would also book an appearance in the FA Cup final against Manchester United, and Jose Mourinho would pull one over on his friend and rival Sir Alex Ferguson once more as Didier Drogba was again the clutch performer with a 116th minute goal in extra time.

2009-10: A League Record and Double

Chelsea made Premier League history in 2009-10 under the leadership of former AC Milan manager Carlos Ancelotti. The Italian tactician brought the best out of all of Chelsea's veterans and youngsters as the Blues scored an EPL record 103 goals in their quest for a return to the top of the league.

Not only was the EPL title counted in their spoils, but so would be their second straight FA Cup title, this time defeating Portsmouth as Pompey had hoped for a final send off before their downfall into both the Championship and administration was complete.

2011-12: Roberto Di Magnifico

Chelsea looked to 2011-12 as the beginning of a new era for the Blues. Roman Abramovich had once again plucked the best and brightest Portuguese managerial talent he could find at FC Porto in former Chelsea assistant to Jose Mourinhio, Andre Villas-Boas.

Villas-Boas had just led Porto to a Portuguese title and UEFA Europa League victory in almost the same fashion as his former manager did before his move to Stamford Bridge in 2004.

The Blues got their season off to a positive start, but by Christmas time it was falling apart, and despite Abramovich trying his hardest to not pull the trigger, he was finally forced to say enough was enough as he relieved AVB from the managerial post in March.

In marched former Blues hero, and former West Bromwich Albion boss, Roberto Di Matteo. With the outlook bleak, Abramovich hoped that Di Matteo could hold the ship together, but no one expected what would ensue over the last two months of the season.

As he took the helm, his first order of business was to lead the club to a dramatic second leg victory over Napoli at Stamford Bridge to see the Blues maintain their place in the UEFA Champions League, and see them progress into the quarterfinals.

The hot streak continued as improved league results also saw the club defeat Tottenham in the FA Cup semifinals to book a place in another FA Cup final of the new millennium.

The Blues would continue their storybook run as their next opponent in the Champions League to fall over two legs would be Portuguese club Benfica. However, no one would expect their next two leg upset to see off defending Champions League winners FC Barcelona 3-2 on aggregate.

Roberto Di Matteo would warm up for his club's Champions League final with an FA Cup title in a 2-1 victory over a hard fighting Liverpool squad.

As the Blues traveled to their next final in Germany to face off against Bavarian giants Bayern Munich in their home stadium, the odds seemed stacked against the club once more.

It seemed like it just might all come crashing down as Thomas Muller scored in the 83rd minute, but in perhaps his most dramatic comeback moment for the Blues, the club's talisman Didier Drogba delivered just five minutes later with a powerful headed effort to draw the match level and force extra time and a penalty shootout that none other than Drogba himself would decide.