The present invention provides a computer-implemented software tool that is adapted to listen continuously to data streams from a drilling operation and to process the data to generate a situation description for a current drilling situation in a form useful for automated continuous matching with a set of past cases stored in a knowledge database. The invention implements a case-based reasoning (CBR) approach to match the current drilling situation as defined by the situation description with one or more stored past cases having a degree of similarity above a predetermined threshold level. Matching cases are displayed to the drilling engineer as symbols on a case “radar”, allowing the drilling engineer to retrieve and view the details of a past case and take appropriate action based on drilling advice provided within the past case.