I am not sure, but months ago I installed Skype in Ubuntu and it automatically pulled chat history from the cloud which means it did.
However, lately my hard disk installed with Windows 7 broke. Now I am using my old backup HDD, which has Windows 7 and Skype already installed, but no matter how I try to retrieve chat history it couldn't?
Answer
No they don't.
Skype archives your chats for you and stores them locally on your computer, if you have enabled this option. Chat histories are not stored anywhere on the Skype network. In other words, no one else will ever be able to see any of your chat histories except you and the person you are chatting with.
(source)
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