Chronic subdural hematoma (CSDH) is a frequent neurosurgical issue, but ischemic cerebrovascular accidents (CVA) following surgery for CSDH are rare and present significant clinical challenges, especially in patients requiring oral anticoagulation (OAC). This case describes an 87-year-old male with atrial fibrillation who developed acute right-sided weakness and aphasia due to an M2 segment occlusion of the left middle cerebral artery (MCA), two weeks after bilateral CSDH evacuation and OAC cessation (the "Apixaban Gap"). The patient underwent successful mechanical thrombectomy with TICI 3 reperfusion, demonstrating marked clinical improvement and favourable functional recovery within three months. This case underscores the risks associated with perioperative anticoagulant interruption in high-risk patients and highlights the therapeutic dilemma in managing concurrent hemorrhagic and thrombotic complications. The technical feasibility and benefit of mechanical thrombectomy for medium vessel occlusions (MeVO) in the post-neurosurgical context are discussed. Ultimately, the case supports individualized, multidisciplinary decisions for early intervention and timely re-initiation of OAC, showing that neither advanced age nor recent neurosurgical history should be absolute contraindications to life-saving stroke interventions when stringent selection and rapid workflows are maintained.