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To smoothen the power fluctuation of the grid, various smart control methods, e.g. vehicle-to-grid (V2G), are developed to rearrange charging and discharging behaviors of Electric Vehicles (EVs) for peak shaving and valley filling. In this paper, a rolling global optimization method is proposed to control the charging/discharging behavior of the EV fleet. Coupled with thorough EV behavior simulation through a trip chain model, the optimization results are more trustworthy and the optimized charging/discharging arrangement could flatten the fluctuation of the grid observably. It proves that the proposed rolling global optimization method could solve the multi-period optimization problem resulted from the uncertainty of EV behavior.