Effective urban warfare training requires situational awareness and muscle memory, developed through repeated practice in realistic yet controlled environments. A key drill, Enter and Clear the Room (ECR), demands threat assessment, coordination, and securing confined spaces. The military uses Synthetic Training Environments that offer scalable, controlled settings for repeated exercises. However, automatic performance assessment remains challenging, particularly when aiming for objective evaluation of cognitive, psychomotor, and teamwork skills. Traditional methods often rely on costly, intrusive sensors or subjective human observation, limiting scalability and accuracy. This paper introduces a video-based assessment pipeline that derives performance analytics from training videos without requiring additional hardware. By utilizing computer vision models, the system extracts 2D skeletons, gaze vectors, and movement trajectories. From these data, we develop task-specific metrics that measure psychomotor fluency, situational awareness, and team coordination. These metrics feed into an extended Cognitive Task Analysis (CTA) hierarchy, which employs a weighted combination to generate overall performance scores for teamwork and cognition. We demonstrate the approach with a case study of real-world ECR drills, providing actionable, domain specific metrics that capture individual and team performance. We also discuss how these insights can support After Action Reviews with interactive dashboards within Gamemaster and the Generalized Intelligent Framework for Tutoring (GIFT), providing intuitive and understandable feedback. We conclude by addressing limitations, including tracking difficulties, ground-truth validation, and the broader applicability of our approach. Future work includes expanding analysis to 3D video data and leveraging video analysis to enable scalable evaluation within STEs.