This paper addresses the quantification of operating reserves in power systems with high penetration of wind power, highlighting challenges due to the intermittency and volatility of wind generation. It employs Monte Carlo simulations and generalized extreme value (GEV) theory to model extreme wind power scenarios that impact operational reliability, proposing a mixed-integer linear quadratic optimization approach for day-ahead dispatching. The methodology is tested using the IEEE 118 bus test system, demonstrating the need for adequate reserves to ensure system reliability amidst uncertainty in wind power forecasts.