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In this paper, we study two closely related airline planning problems: the robust weekly aircraft maintenance routing problem (RWAMRP) and the tail assignment problem (TAP). In real life operations, the RWAMRP solution is used in tactical planning whereas the TAP solution is implemented in operational planning. The main objective of these two problems is to minimize the total expected propagated delay (EPD) of the aircraft routes. To formulate the RWAMRP, we propose a novel weekly line-of-flights (LOF) network model that can handle complex and nonlinear cost functions of EPD. Because the number of LOFs grows exponentially with the number of flights to be scheduled, we propose a two-stage column generation approach to efficiently solve large-scale real-life RWAMRPs. Because the EPD of an LOF is highly nonlinear and can be very time-consuming to accurately compute, we propose three lower bounds on the EPD to solve the pricing subproblem of the column generation. Our approach is tested on eight real-life test instances. The computational results show that the proposed approach provides very tight LP relaxation (within 0.6% of optimal solutions) and solves the test case with more than 6000 flights per week in less than three hours. We also investigate the solutions obtained by our approach over 500 simulated realizations. The simulation results demonstrate that, in all eight test instances, our solutions result in less EPDs than those obtained from traditional methods. We then extend our model and solution approach to solve realistically simulated TAP instances. [ABSTRACT FROM AUTHOR]