This study explores the link between the monotonic and cyclic undrained behaviour of sands using the discrete element method (DEM). It is shown that DEM can effectively capture the flow deformation of sands sheared under both monotonic and cyclic undrained loading conditions. When subjected to cyclic shearing, flow-type failure is observed for a loose sample, while cyclic mobility is observed for a dense sample. A strong correlation between the monotonic and cyclic loading behaviour that has been revealed experimentally is also confirmed in DEM simulations: (a) flow deformation occurs in the compressive loading direction when the cyclic stress path intersects the monotonic compression stress path prior to the monotonic extension stress path, and vice versa; (b) the onset of flow deformation in q– p′ space is located in the zone bounded by the critical state line and the instability line determined from monotonic simulations. Hill’s condition of instability is shown to be effective to describe the onset of flow failure. Micro-mechanical analyses reveal that flow deformation is initiated when the index of redundancy excluding floating particles drops to below 1.0 under both monotonic and cyclic loading conditions. Flow deformation induced by either monotonic or cyclic loading is characterized by an abrupt change of structural fabric which is highly anisotropic. The reason why the dense sample dilated during monotonic loading but showed cyclic mobility (temporary liquefaction) during cyclic loading is attributed to the repeating reversal of loading direction, which leads to the periodic change of microstructure.