The future of Avram Grant and several of the club's stars is under the spotlight again after Chelsea finished second best to Manchester United.
The Blues were runners-up in the Champions League final only 10 days after suffering the same fate in the Premier League.
Grant, who steered the club out of crisis and to the final of European club football's elite competition for the first time, is still not secure in his position as the summer approaches.
Their failure to wrest the title from United's grasp on a dramatic last day of league action, before missing out in Moscow, will inevitably spark more speculation that the Israeli will move back 'upstairs' at Stamford Bridge.
His replacement, as has been suggested ever since Jose Mourinho was axed last September, may be Frank Rijkaard if owner Roman Abramovich opts to make another managerial change.
Rijkaard is leaving Barcelona after five years in charge at the Nou Camp and west London could be his destination.
But, apart from Grant's position, Chelsea face numerous problems with a squad which, quite remarkably, took them from fifth in the table when Mourinho was axed to the brink of winning the title.
It will require severe pruning and strengthening if Chelsea are to be a force on the domestic and European fronts again next season.
Even reaching the final in Moscow will not stop certain players from being shown the exit door. Others will depart of their own choosing.
Among the fringe players that Chelsea will consider are surplus to requirements are midfielder Steve Sidwell and striker Claudio Pizarro.
Both players were not considered good enough for the Champions League squad and Sidwell has yet to demonstrate he is consistently good enough at the highest level.
Pizarro was a complete disappointment from the moment he arrived. While the striker is robust enough for English football, he lacks the pace required to trouble defences.
Among those likely to ask to leave are England winger Shaun Wright-Phillips. He is already unhappy with being a bit-part player during the all-important run-in and was totally overlooked in the Champions League semi-final legs against Liverpool and the final against United.
Andriy Shevchenko may not ask to go but may seek sanctuary back at AC Milan for the rest of his career.
Florent Malouda admits he has found it hard to adapt to the Premier League but there are signs he is improving. He may well opt to stay and Grant, if he remains as manager, could get the best out of the wayward French winger.
But the biggest worries for the club concern the futures of midfielder Frank Lampard and striker Didier Drogba.
The death of Lampard's mother Pat could be a decisive factor for the England international when it comes to making up his mind about staying.
Talks over a new, long-term contract, have been on hold all season despite Lampard appealing for his future to be sorted out.
Despite denials of an agreement with Inter Milan, the loss of his mother may well provide the catalyst for him to seek out new pastures because there are too many memories for him at Stamford Bridge.
Drogba's situation depends on the club's willingness to cash in on a player who continues to prove his worth on the pitch.
Drogba's future has been the subject of constant speculation all season and the Ivorian even said he wanted to follow Mourinho out of the club at one stage.
He has two years left on his current contract but if the right offer arrived, then Chelsea may well opt to take the cash and use it to get the kind of players Grant and his management team want.
Rebuilding the squad is going to be tough and expensive. Kaka and Lionel Messi are just two of the big names already linked with the club but a more realistic option would be to move for Tottenham striker Dimitar Berbatov.
Chelsea were interested in him during the January transfer window but Spurs' asking price of £30million was just a tad too high, even for Abramovich.
Blackburn's Roque Santa Cruz is another striker who would fit Grant's attacking ambitions.
He enjoyed a fabulous first season at Blackburn but would now cost Chelsea far more than the £3.8million Rovers paid for him.
Porto defender Jose Bosingwa, 25, has already been signed for £16m. Bosingwa is a fast, overlapping right-back who has broken into the Portugal side in recent seasons and that could spell the end for Juliano Belletti. Bosingwa's fellow right-back and compatriot Paulo Ferreira signed a five-year contract earlier this season.
Grant admits that money is no object and Chelsea have already identified their targets. But whether or not he gets his men will largely depend on whether he remains as manager.
It is going to be an interesting summer at Stamford Bridge.


CFC1905 (Chelsea) : "...jess/chelseatillI die - I agree with you both about the speed of our attacks, however, if there are no options available then it is better to hold the ball rather than simply hoof it up the pitch. For me, variation, is w..." view full comment
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