Background <p>Gestational trophoblastic neoplasia (GTN) encompasses a rare group of trophoblastic malignancies, typically diagnosed clinically. Histopathology plays a pivotal role in resolving diagnostically challenging cases, as highlighted in this case series.</p> Methods <p>We reviewed nine cases of GTN evaluated histopathologically at the Department of Pathology, St. John’s Medical College, Bangalore (January 2013–December 2024).</p> Results <p>Patients were predominantly of reproductive age, with one exception (48&#xa0;years). Vaginal bleeding was the most common presenting symptom (<i>n</i> = 6). Gestational choriocarcinoma (GC) was the most frequent diagnosis (<i>n</i> = 5, 60%), including four high-risk and one ultrahigh-risk case. Miscarriage was the antecedent gestation in 60% of GC cases. Histopathology confirmed GTN in one clinically unsuspected patient with a lung mass and low β-hCG. Surgery was typically indicated for failed chemotherapy, and two patients succumbed to the disease.</p> <p>Intermediate trophoblastic tumors (<i>n</i> = 4) comprised placental site trophoblastic tumor (PSTT, <i>n</i> = 2), epithelioid trophoblastic tumor (ETT, <i>n</i> = 1), and a mixed PSTT-ETT tumor (<i>n</i> = 1). These cases followed term pregnancies in 75%, with diagnosis intervals ranging from 12 to 144&#xa0;months. Uncontrolled bleeding or failed chemotherapy necessitated surgery. Notably, the patient with ETT presented with multiple fistulas, a clinically unsuspected case, diagnosed as GTN on histopathology. The mixed tumor, initially diagnosed as PSTT, revealed an additional ETT component on hysterectomy.</p> Conclusion <p>This case series highlights the diverse clinical and pathological spectrum of GTN and emphasizes the role of histopathology in challenging diagnostic scenarios. Accurate diagnosis aids in tailoring management strategies, ensuring prompt and effective treatment, and improving clinical outcomes.</p>