In this paper, we introduce a pilot's scheduling model which is able to maintain and balance their capabilities for each relevant skill level in military helicopter squadron. Flight scheduler has to consider many factors related pilot's flight information and spends a lot of times and efforts for flight planning without scientific process depending on his/her own capability and experience. This model reflected overall characteristics that include pilot's progression by basis monthly and cumulative flight hours, operational recent flight data and quickly find out a pinpoint areas of concern with respect to their mission subjects etc. There also include essential several constraints, such as personnel qualifications, and Army helicopter training policy's constraints such as regulations and guidelines. We presented binary Integer Programming (IP) mathematical formulation for optimization and demonstrated its effectiveness by comparisons of real schedule versus model's solution to several cases experimental scenarios and greedy random simulation model. The model made the schedule in less than 30 minutes, including the data preprocessing process, and the results of the allocation were more equal than the actual one. This makes it possible to reduce the workload of the scheduler and effectively manages the pilot's skills. We expect to set up and improve better flight planning and combat readiness in Korea Army aviation.