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Introduction For patients presenting with neurological changes from pituitary tumor apoplexy, urgent surgical intervention is commonly performed for diagnosis, tumor resection, and optic apparatus decompression. Although identification and preservation of the pituitary gland during the time of surgery can be challenging, it may lead to improve endocrine outcomes. Methods A retrospective case series of all patients with macroadenomas presenting with apoplexy at Loyola University Medical Center from 2016 to 2018 was studied. Demographic, radiographic, and intraoperative characteristics were collected including age, gender, comorbidities, presenting symptoms, preoperative size of pituitary adenoma, Knosp's grade, Hardy's grade, identification and/or preservation of the gland, pre- and postoperative hormonal levels, intraoperative and/or postoperative complications, and follow-up time. Results A total of 68 patients underwent endoscopic endonasal surgery for resection of a macroadenoma. Among them, seven (10.2%) presented with apoplexy; five patients were male and two were female and presenting symptoms and signs included headache (100%), endocrinopathies (57%), visual acuity deficit (71%), visual field deficit (71%), and oculomotor palsy (57%). A gross-total resection rate was achieved in 86% of patients. Among them, 71% of patients obtained complete symptomatic neurological improvement. A statistically significant difference between gender and endocrine function was found, as no females and all males required some form of postoperative hormonal supplementation (p = 0.047). Conclusion Endoscopic endonasal resection of macroadenomas with sparing of the pituitary gland in the setting of apoplexy is safe and effective. Preservation of the normal gland led to no posterior pituitary dysfunction, and a statistically significant difference between gender and postoperative endocrinopathy was identified. Further studies with larger samples sizes are warranted.