In this paper, theoretical derailment equations for cross-wind with frequency were derived to assess running safety. For a KTX (Korean high-speed train) unit, the wheel unloading ratios, which are the criteria for evaluating derailments in UIC (International union of railways) and TSI (Technical Specification for Interoperability) regulations, were calculated through the formula under the driving regulations according to cross-wind speeds, and the theoretical results were compared and evaluated through a multibody dynamics (MBD) simulation. In addition, the wheel unloading ratios were calculated for various frequencies of cross-winds. As a result of the formula and MBD, the wheel unloading ratios were shown to increase rapidly regardless of the dampers in suspension when the cross-wind frequency and the natural frequency of a vehicle were in agreement. Finally, we calculated the changes of wheel unloading ratio for different track gauges and found that these theoretical equations could calculate more accurate results than the existing Kunieda’s formula. The formula derived in this study has the advantage of considering various variables, such as fluctuant cross-winds, rail irregularities, and derailment behaviors, which were not considered in previous studies or Kunieda’s formula. It could be used for setting suspensions or railway vehicle specifications in the initial design stage.