“We’ve all been there, you send someone a question and just as you hit enter you figure out the answer for yourself,” he writes. It’s easy to remove a single message, including one you haven’t yet sent. He provides instructions on how to do all those things in a new post. Over at Skype’s Tips & Tricks blog, Matthew de Beer says he often sees questions from users who want to know how to delete individual messages, entire chats or even the contents of Skype Home. How to Delete Conversations on Skype on a PC or Mac In this Article: Deleting an Entire Conversation Deleting Individual Messages Community Q&A This wikiHow teaches you how to delete both entire Skype conversations and individual Skype messages on your PC or Mac. Right-click the contact name in the sidebar of the Skype window and choose “Delete. In Skype for Mac OS X, you can delete all the conversation history for just one specific Skype contact. Your device must be connected to an internet so the command would directly update the Skype cloud. To delete the messages, select a particular message and click with two fingers on your trackpad, the option to delete the message should show. Skype For Business Mac Delete Conversations.