Generally described are systems and methods for conducting content differential analysis on multiple versions of an item, such as a book published with multiple editions or an item released with multiple versions. A version similarity scoring system may be configured to perform such content differential analysis on item content between two or more versions, and generate one or more similarity scores or assessments between versions. Similarity scores may be generated for the item as a whole as well as for some or all particular content portions or features of the item. The similarity scores for various versions may be provided to consumers viewing item detail pages for a multi-version item, as well as to vendors as part of purchase planning and market price setting decision processes.