In mechanised tunnelling, a thorough scheduling of the maintenance processes for cutting tool changes is necessary to ensure the economic success of the project. Therefore, a maintenance scheduling method has been developed, which considers the uncertain wear prediction of the cutting tools as well as the project-specific boundary conditions. Process simulation is used to model and analyse the wear of cutting tools and to evaluate different maintenance strategies. The input of costs factors allows for an estimation of maintenance costs. Monte Carlo Simulations are conducted to consider uncertain input data. Sensitivity analyses are conducted in order to increase the knowledge of the system behaviour and dependencies. Based on the conducted analyses, a procedure to schedule and improve the maintenance of cutting tools is recommended using the proposed model.