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Kent batsmen Martin van Jaarsveld and Joe Denly have both left the club.
Denly's departure was expected as he failed to agree terms on a new deal with Kent and has joined newly-promoted Middlesex.
But the exit of van Jaarsveld will send alarm bells ringing throughout the county's supporters after he was released from his contract which still had 12 months to run.
The South African-born batsmen, who was awarded his county cap in 2005, was heavily linked with a move to Lancashire last summer but he has opted to join strugglers Leicestershire, the only team who finished below Kent in Division 2 of the LV= County Championship.
Van Jaarsveld said: "I have poured everything I have had in to trying to score runs and win games for the county during this time, but now it is time for a new challenge which I hope will reignite my passion for the game and allow me to recapture my best form."
Denly, who played one-day international cricket for England in 2009, struggled for runs this summer despite a late upturn in form which included a century against the touring India side.
""A large part of me is very sad to be leaving Kent," said Denly. " As a local lad who’s come through the system I expected to play my whole career here.
"This is an important stage of my career, however, and I’m really excited about the move to Middlesex, who are a club on the up as shown by their recent promotion to division one of the Championship.
" I’m committed to becoming the best player I can possibly be and firmly believe that the environment at Middlesex will help me achieve that and one day resurrect my prospects at international level.
"I’d like to thank everyone at Kent, particularly my captain Rob Key, for the support I’ve received over the last 8 years - and who knows what the future holds, I’d certainly never rule out a return to the club one day."
Kent chairman of cricket Graham Johnson said: "Martin approached the club at the end of the season with a desire to be released from contract and after much consideration the club decided to agree to that request.
"Joe developed through the Kent system and the club had hoped to keep him, but he decided it was time for a fresh challenge.
"We wish both players well as they move on and thank them for their efforts for the county."