The incidence of cancer among pregnancy, albeit rare, presents as a significant diagnostic challenge for clinicians especially with considerations for materno-fetal well-being. The double-edged sword of Renal Clear Cell Carcinoma and Gastrointestinal Stromal Tumor in near-term pregnant woman was encountered in our case and skillfully maneuvered via combination of advanced diagnostic techniques involving CT, MRI and endoscopy. A discussion board comprising of experts was set up and after extended consultation involving patient's relatives, elective cesarean was performed at 34 weeks after which surgical excision resulted in successful extraction of both the tumors, ensuring the survival of both mother and child.