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Objective: The most common surgical technique for the management of pituitary adenomas is the endoscopic endonasal transsphenoidal approach (EEA). preoperative neuroimaging along with detecting surgical landmarks of the sphenoid sinus during surgery is important for making a successful operation., Method: This study includes 1009 patients with pituitary adenomas who underwent EEA between 2013 and 2020. We evaluated the anatomical features of the sphenoid sinus through a panel of items obtained from imaging and intra-operative findings., Results: Our result includes 57.38% nonfunctional, 8.42% cushing, 12.39% prolactinoma, and 21.8% acromegaly patients who had undergone endoscopic endonasal transsphenoidal surgery. The mean age of the patients was 45 with a male to female ratio of 1.2:1. Sellar sphenoid type was the most common (91.8%) with only 12% symmetrical inter sphenoid septa, Internal carotid artery dehiscence was found in 1.7% of the cases. Apoplexy was present in 6.3% of patients, which was found more prevalent in nonfunctional adenomas (9.67%, Odds ratio: 4.85, 95% CI 2.24-11.79) and further investigation revealed a significant association between apoplexy and sphenoid mucosal edema and hemorrhage (Odds ratio: 43.0, 95% CI 22.50-84.26), and between apoplexy and cystic lesions (OR = 4.14, 95% CI 1.87-8.45, P-value < 0.0001). Acromegaly is associated with the increased number of lateral recces (Odds ratio: 11.41, 95% CI 7.54-17.52), septation of the sphenoid sinus (Marginal mean: 3.92, 95% CI 3.69-4.14), edematous sinonasal mucosa (Odds ratio: 6.7; 95% CI 4.46-10.08), and higher bony (OR: 4.81, 95% CI 2.60-8.97, P-value < 0.001) and cavernous (OR: 1.7, 95% CI 1.13-2.46, P-value < 0.01) invasion., Conclusion: The present study provides anatomical data about the sphenoid sinus and its adjacent vital structures with adenomal specific changes that are necessary to prevent complications during endoscopic advanced transsphenoidal surgery., (© 2023. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.)