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Due to the high penetration of renewable energy into the energy matrix of today's power networks, the design of generating systems based only on static reserve assessment does not seem to be enough to guarantee the security of power system operation. From the wind power integration perspective, this energy source imposes additional requirements, mainly due to the inherent unpredictable characteristic of the wind. Besides the uncertainties in load and generating unit availabilities, the operating reserve needs also to deal with the fluctuation characteristic of the wind power. Therefore, more flexibility of the conventional generators (hydro and thermal) is required to provide system support services. This paper discusses a new methodology based on chronological Monte Carlo simulation to evaluate the operating reserve requirements of generating systems with large amounts of renewable energy sources, in particular, wind power.