Content generation that is both relevant and up to date with the current threats of the target audience is a critical element in the success of any Cyber Security Exercise (CSE). Through this work, we explore the results of applying machine learning techniques to unstructured information sources to generate structured CSE content. The corpus of our work is a large dataset of publicly available cyber security articles that have been used to predict future threats and to form the skeleton for new exercise scenarios. Machine learning techniques, like named entity recognition (NER) and topic extraction, have been utilised to structure the information based on a novel ontology we developed, named Cyber Exercise Scenario Ontology (CESO). Moreover, we used clustering with outliers to classify the generated extracted data into objects of our ontology. Graph comparison methodologies were used to match generated scenario fragments to known threat actors' tactics and help enrich the proposed scenario accordingly with the help of synthetic text generators. CESO has also been chosen as the prominent way to express both fragments and the final proposed scenario content by our AI-assisted Cyber Exercise Framework (AiCEF). Our methodology was put to test by providing a set of generated scenarios for evaluation to a group of experts to be used as part of a real-world awareness tabletop exercise.