The impact of surface flux boundary conditions and geostrophic forcing on multiday evolution of flow in the atmospheric boundary layer (ABL) was assessed using large-eddy simulations (LES). The LES investigations included several combinations of surface boundary conditions (temperature and heat flux) and geostrophic forcing (constant, time varying, time and height varying). The setup was based on ABL characteristics observed during a selected period of the Cooperative Atmosphere–Surface Exchange Study—1999 (CASES-99) campaign. The LES cases driven by a constant geostrophic wind achieved the best agreement with the CASES-99 observations specifically in terms of daytime surface fluxes and daytime and nighttime profiles. However, the nighttime fluxes were significantly overestimated. The LES cases with the surface temperature boundary condition and driven by a time- and height-varying geostrophic forcing showed improved agreement with the observed nighttime fluxes, but there was less agreement with other observations (e.g., daytime profiles). In terms of the surface boundary condition, the LES cases driven by either surface temperature or heat fluxes produced similar trends in terms of the daytime profiles and comparisons with data from soundings. However, in reproducing the fluxes and nighttime profiles, the agreement was better with imposed temperature because of its ability to interact dynamically with the air temperature field. Therefore, it is concluded that surface temperature boundary condition is better suited for simulations of temporally evolving ABL flow as in the diurnal evolution of the ABL.