This work addresses the cockpit crew training scheduling problem. The objective is to produce a robust cockpit crew training schedule, including the assignment of trainees, instructors and simulators. To attain this objective, we propose a scheduling framework composed of four modules: a Training Scheduling & Assignment Model (TS&AM), a Disruption Generator (DG), a Rule-Based Recovery (RBR) algorithm, and a Neural Network (NN). The TS&AM is an integer programming model that integrates the scheduling of courses and the assignment of resources. The output roster serves as input for a data-driven DG based on Monte-Carlo Simulation. The disruptions are then solved using the RBR algorithm. Finally, The NN feedback algorithm learns the recovery costs experienced in the disruption impact simulator and updates these costs in the TS&AM to generate more robust rosters. The proposed modelling framework was calibrated, tested, and demonstrated in a simulation environment developed using four years of historical crew training data from a major European airline. The experiment showed that our approach outperformed the roster produced by the airline. The approach proposed produces rosters that reduce recovery costs by 21 percent, while still decreasing total training costs by 3 percent.