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This case report highlights the diagnostic and therapeutic journey of a 16-year-old female presenting with chronic headaches, ultimately diagnosed with anaplastic meningioma. Despite its rarity in pediatric patients, anaplastic meningioma necessitates swift recognition and management due to its aggressive nature. Imaging findings, including CT and MRI, initially suggested a provisional diagnosis of hemangiopericytoma, emphasizing the diagnostic challenge posed by this condition. Surgical intervention revealed unexpected histopathological findings, highlighting the importance of thorough evaluation. Treatment involved frontal craniectomy and excision followed by adjuvant radiotherapy. While the patient's postoperative course was uneventful, histopathology confirmed the presence of anaplastic meningioma, leading to the adjustment of her clinical management. This case shows the need for heightened suspicion and comprehensive evaluation in similar presentations to facilitate timely intervention and improve patient outcomes.