Large-scale companies across various sectors maintain substantial IT infrastructure to support their operations and provide quality services for their customers and employees. These IT operations are managed by teams who deal directly with incident reports (i.e., those generated automatically through autonomous systems or human operators). (1) Background: Early identification of major incidents can provide a significant advantage for reducing the disruption to normal business operations, especially for preventing catastrophic disruptions, such as a complete system shutdown. (2) Methods: This study conducted an empirical analysis of eleven (11) state-of-the-art models to predict the severity of these incidents using an industry-led use-case composed of 500,000 records collected over one year. (3) Results: The datasets were generated from three stakeholders (i.e., agency, customer, and employee). Separately, the bidirectional encoder representations from transformers (BERT), the robustly optimized BERT pre-training approach (RoBERTa), the enhanced representation through knowledge integration (ERNIE 2.0), and the extreme gradient boosting (XGBoost) methods performed the best for the agency records (93% AUC), while the convolutional neural network (CNN) was the best model for the rest (employee records at 95% AUC and customer records at 74% AUC, respectively). The average prediction horizon was approximately 150 min, which was significant for real-time deployment. (4) Conclusions: The study provided a comprehensive analysis that supported the deployment of artificial intelligence for IT operations (AIOps), specifically for incident management within large-scale organizations.