Accurate prediction of low-occurrence wind speeds around urban structures is crucial for safe building design. Although Large-eddy simulation (LES) is commonly used as a high-fidelity model as compared with the Reynolds-Averaged Navier–Stokes (RANS) simulations, the present validation process relies on the comparison of fundamental statistics of the mean and standard deviations. The discrepancies in LESs and wind-tunnel experiments (WTEs) are unclear in terms of physical quantities characterizing the unsteadiness of the simulated turbulent flow such as probability density and power spectral densities, and low-occurrence winds speeds. Therefore, this study aims to evaluate the effectiveness of LES in predicting unsteady wind behavior around a 1:1:2 block model. The study identifies prominent differences to improve the accuracy of unsteady numerical simulations especially for the purpose of predicting low-occurrence wind speeds. Various advection schemes in LESs were investigated, including first-order upwind, second-order linear, and dynamic interpolation schemes. The results show significant discrepancies, particularly in higher-order statistics and low-occurrence wind speeds, with WTE consistently exhibiting higher energy levels across all frequencies. These findings highlight the need to refine advection schemes to enhance their predictive accuracy. LESs with minimal numerical errors from discretization schemes can substantially improve urban wind assessments and contribute to the design of safer structures.