The present disclosure is directed to a system and method for controlling a wind farm. The method includes operating the wind farm based on multiple control settings over a plurality of time intervals. A next step includes collecting one or more wind parameters of the wind farm over the plurality of time intervals and one or more operating data points for each of the wind turbines in the wind farm for the plurality time intervals. The method also includes calculating a contribution of the operating data points for each of the wind turbines as a function of the one or more wind parameters. Further steps of the method include estimating an energy production for the wind farm for each of the control settings based at least in part on the contribution of the operating data points and controlling the wind farm based on optimal control settings.