Skype offers a way to delete the complete chat history of every contact and to change the time period in which the chat history is kept. It leaves the user clueless however on how to remove the chat history with one contact only and the official answer from Skype is that it is not possible to delete the chat history of one contact.

This is only partially correct. There is no easy way to clear the chat history but there is one. Skype saves all chats with contacts in a Skype folder in Documents & Settings. The full path would be C:\Documents and Settings\username\Application Data\Skype\skype username.

In there you find the databases chatmsg256.dbb, chatmsg512.dbb, chatmsg1024.dbb, chatmsg2048.dbb, chatmsg4096.dbb and chatmsg8192.dbb. Those files contain your chat history. Unfortunately though those are not sorted by contact but by length.

This means that you would have to open each of the files and look for the lines of the contact that you want to delete. What makes things worse is that there will be lots of garbage in the text editor and that it is not always obvious who the chat contact of the current line is.

The best approach in my opinion would be to make copies of the files and work with them. You can’t open the originals if Skype is open and you do need Skype to look at the chat history and search for the phrases in those files.

It is lots of work but the only working way of clearing the chat history of one contact in Skype.