Introduction: A supraorbital keyhole craniotomy (SOKC) is a novel alternative to frontal craniotomies for accessing the anterior fossa for resecting tumors and clipping aneurysms; however, its implementation is limited in patients at a high risk of complications. We present two cases involving the use of augmented reality (AR) and virtual reality (VR) for patient selection and preoperative planning for a supraorbital tumor resection of anterior fossa meningiomas. Methods: This is a prospective, single-center case series at a research institute. We identified patients with an anterior or middle fossa meningioma regardless of age, gender, and tumor characteristics who could undergo an SOKC and MRI. The preoperative planning was performed with the BrainLab Magic Leap AR/VR platform. The meningiomas were resected through the SOKC under neuronavigation. Results: We identified two cases: a 37-year-old male with a meningioma in the sellar region and an 84-year-old male with a right anterior fossa meningioma, both confirmed by MRI. Both patients had a complete tumor resection by a minimally invasive SOKC after preoperative planning with the AR/VR platform. Postoperatively, hyponatremia complicated the first case, while the second case developed an intracranial hemorrhage. They both recovered after the appropriate interventions. Conclusions: The use of an SOKC for anterior skull base meningiomas should be individualized after considering the lesion characteristics, vascular control needs, and the surgeon’s expertise. VR/AR-assisted preoperative evaluation and planning will optimize the patient selection and surgical outcomes. We can utilize VR/AR technologies to identify patients that will benefit from an SOKC and expand the implementation of the approach beyond its current limitations.