Endoscopic pituitary adenoma surgery has a steep learning curve, with varying surgical techniques and outcomes across centers. In other surgeries, superior performance is linked with superior surgical outcomes. This study aimed to explore the prediction of patient-specific outcomes using surgical video analysis in pituitary surgery. Endoscopic pituitary adenoma surgery videos from a single center were annotated by experts for surgical workflow (3 phases, 15 steps) and surgical skill (using modified Objective Structured Assessment of Technical Skills; mOSATS). Quantitative workflow metrics were calculated, including phase duration and step transitions. Poisson or logistic regression was used to assess the association of workflow metrics and mOSATS with common inpatient surgical outcomes. 100 videos from 100 patients were included. Nasal phase mean duration was 24mins and mean mOSATS was 21.2/30. Mean duration was 34mins and mean mOSATS was 20.9/30 for the sellar phase, and 11mins and 21.7/30 respectively for the closure phase. The most common adverse outcomes were new anterior pituitary hormone deficiency (n=26), dysnatremia (n=24) and cerebrospinal fluid (CSF) leak (n=5). Higher mOSATS for all three phases and shorter operation duration was associated with decreased length of stay (p=0.003 & p<0.001). Superior closure phase mOSATS were associated with reduced post-operative CSF leak (p<0.001), and superior sellar phase mOSATS were associated with reduced post-operative visual deterioration (p=0.041). Superior surgical skill and shorter surgical time were associated with superior surgical outcomes, at a generic and phase-specific level. Such video-based analysis has promise for integration into data-driven training and service improvement initiatives.