From the transfer ban, to their hot start out of the gates, and lastly, the announcement of Peter Kenyon's departure, the club has experienced a roller coaster ride.
Petr Cech told the Guardian that the team is not experiencing any more pressure than usual.
Despite a lackluster performance in their match against FC Porto on September 15, the Chech international is confident that the team can excel in the Champions League this season.
The Pressure Has Always Been There.
In 2005, when Jose Mourinho was brought in to manage the club, his experience winning the Champions League was expected to trickle down to the west London team.
However, Mourinho was never able to secure the title and that led to the rotating manager situation that has pervaded the club in recent years.
Much like Mourinho, no manager has brought the trophy back to Stamford Bridge.
Avram Grant was the closest, leading them team to the final in 2007.
The arrival of Guus Hiddink saw a return to the way Chelsea played prior to Mourinho's departure and the pressure was on for the team to advance to the final. Once again, they were denied.
However, Hiddink's departure brought about another managerial change for Chelsea and speculation that the squad would return to their inconsistent ways.
Carlo Ancelotti took the helm at the start of the 2009 season and so far the team has been in top form. Ancelotti has the Champions League akin to what Mourinho brought to the club.
However, Ancelotti also won the trophy as a player as well.
But Is Ancelotti The Key?
Ancelotti has stated that a return to the final is the minimum expectation for the club this season and with the line up he has, it is certainly a possibility.
Ancelotti's playing career saw two Champions League victories in 1989 and 1990. He earned the title while playing with one of the finest sides AC Milan have fielded.
He then returned to coach Milan where his side won two Champions League titles.
Despite the depth of his trophy case, the end result comes down to the performance of the team.
However, it seems that Ancelotti has tapped into a drive to succeed that was started under Hiddink.
His experience on both sides of the trophy, player and coach, will only help to motivate a Chelsea side that are eager to prove themselves in Europe.
Like Always, There Will Be Pressure
While Cech's comment about not feeling pressure can and should be addressed on a player to player basis, there is certainly pressure on Ancelotti.
The Italian has lived through the football system and is likely aware of the coach courting that Chelsea have went through since the departure of Mourinho.
The pressure that the team isn't feeling is being shifted off to their manager.
Ancelotti knows he has to deliver in Europe or it will be likely that Chelsea owner, Roman Abromavich, will deal him out of the clubs 2010-2011 season for yet another coach.
However, Chelsea are armed with a squad that responds well to Ancelotti's style of coaching and a manager who has fought for the title on the level of a player.
Therefore, the factors are in place to see the pressure removed from Ancelotti with a Champions League victory for Chelsea