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This paper proposes a new methodology based on Monte Carlo chronological simulation to evaluate the operating reserve requirements of generating systems with large amounts of renewable energy sources. The main idea is to build a new probabilistic approach to assess several performance indices bearing in mind the long-term planning. Besides the conventional indices used in generating capacity reliability assessment and also those obtained from the well-being framework, a new set of indices are proposed to measure the availability of different types of operating reserve. The relationship between the proposed approach and the traditional PJM method is also discussed. Renewable in this study mainly comprises wind power sources and for that the IEEE RTS-96 is adapted to illustrate the proposed methodology. Finally, different planning criteria are discussed to deal with the design of generation system capacity, static and operational, in the long-term planning.