Gynaecological disorders constitute a major component of women’s morbidity worldwide, encompassing menstrual irregularities, functional ovarian disorders, uterine pathologies, and psychosomatic reproductive disturbances. While conventional gynaecology largely emphasises hormonal and structural paradigms, homoeopathy approaches gynaecological illness as an expression of constitutional imbalance involving physical, mental, and emotional spheres. Classical homoeopathic Materia Medica offers rich descriptions of female disorders, yet interpretative differences exist among major authors. This narrative literature review comparatively examines the approaches of James Tyler Kent, Cyrus Maxwell Boger, and William Boericke in the understanding and management of gynaecological disorders. Through systematic textual analysis, convergences and divergences in remedy interpretation, symptom valuation, and clinical emphasis are explored. The review highlights how Kent’s mental–emotional hierarchy, Boger’s time–pathology correlation, and Boericke’s clinically concise schema complement each other in gynaecological practice. The synthesis demonstrates that comparative Materia Medica analysis enhances precision in remedy selection and supports individualised prescribing in women’s health.