Background: Human-centric artificial intelligence (HCAI) aims to provide support systems that can act as peer companions to an expert in a specific domain, by simulating their way of thinking and decision-making in solving real-life problems. The gynaecological artificial intelligence diagnostics (GAID) assistant is such a system. Based on artificial intelligence (AI) argumentation technology, it was developed to incorporate, as much as possible, a complete representation of the medical knowledge in gynaecology and to become a real-life tool that will practically enhance the quality of healthcare services and reduce stress for the clinician. Our study aimed to evaluate GAIDS’ efficacy and accuracy in assisting the working expert gynaecologist during day-to-day clinical practice. Methods: Knowledge-based systems utilize a knowledge base (theory) which holds evidence-based rules (“IF-THEN” statements) that are used to prove whether a conclusion (such as a disease, medication or treatment) is possible or not, given a set of input data. This approach uses argumentation frameworks, where rules act as claims that support a specific decision (arguments) and argue for its dominance over others. The result is a set of admissible arguments which support the final decision and explain its cause. Results: Based on seven different subcategories of gynaecological presentations—bleeding, endocrinology, cancer, pelvic pain, urogynaecology, sexually transmitted infections and vulva pathology in fifty patients—GAID demonstrates an average overall closeness accuracy of zero point eighty-seven. Since the system provides explanations for supporting a diagnosis against other possible diseases, this evaluation process further allowed for a learning process of modular improvement in the system of the diagnostic discrepancies between the system and the specialist. Conclusions: GAID successfully demonstrates an average accuracy of zero point eighty-seven when measuring the closeness of the system’s diagnosis to that of the senior consultant. The system further provides meaningful and helpful explanations for its diagnoses that can help clinicians to develop an increasing level of trust towards the system. It also provides a practical database, which can be used as a structured history-taking assistant and a friendly, patient record-keeper, while improving precision by providing a full list of differential diagnoses. Importantly, the design and implementation of the system facilitates its continuous development with a set methodology that allows minimal revision of the system in the face of new information. Further large-scale studies are required to evaluate GAID more thoroughly and to identify its limiting boundaries.