Update from year 2017: The tool described in this post DOES NOT WORK with recent versions of Skype. Either these versions stopped saving removed messages altogether, or they are doing it in a novel manner not recognized by the tool.
In other words - you would only recover "removed" messages if you are running older version of Skype (or these messages were sent at the time you were using that older version).
Yesterday I happened to attend a discussion about the security and privacy of information stored locally in Skype and Thunderbird profiles. It turns out, if you obtain a person's Skype profile directory, you will be able to log in as him without the need to know the password. In addition, Dominique made a remark that Skype does not really delete the messages that are marked as "removed" in the chat window. I found that curious and decided to take a closer look.
Indeed, there is a bunch of *.dat files in the chatsync subdirectory of the Skype's profile, which preserve all messages along with all their edits or deletions. Unfortunately, the *.dat files are in some undocumented binary format, and the only tool I found for reading those lacks in features. However, hacking up a small Python parser according to what is known about the format, along with a minimalistic GUI is a single evening's exercise, and I happened to be in the mood for some random coding.
Skype Chatsync Viewer
Now, if you want to check out what was that message you or your conversation partner wrote before it was edited or deleted, this package will help. If you are not keen on installing Python packages, here is a standalone Windows executable.
