Google, one of the largest and most valuable companies in the world, is being sued for allegedly anticompetitive practises regarding two of its most popular products: its eponymous search engine and the phone operating system Android. The verdicts in these cases have the potential to change Google’s ascendant trajectory, much as it did for another firm that found itself in a similar position some twenty years ago – Microsoft. By analysing Microsoft’s historical lawsuits and building models for specific features found in the technologies and actions of Microsoft, a framework for determining “guilt” in an antitrust case can be developed. Applied to Google, this framework predicts a successful conviction regarding Android, but an unsuccessful one for Google’s search product.