An experimental study is made to understand the deformation characteristics and failure mechanism of sands subjected to severe plastic deformation in the ploughing model setup of in-plane orthogonal cutting. The cutting experiments were performed on sands over 3 orders of strain rates. High-speed imaging and concomitant image analysis were performed using the Particle Image Velocimetry algorithm to obtain the whole field velocity measurements of the material flow. The velocity field maps of the near tool tip region demonstrate a sharp change in the motion of sand particles along with the formation of a dead zone. The effective strain rate maps show regions of intense localized plastic deformation- termed shear bands. The inclination angle of these bands evolved periodically with time and showed a decreasing trend due to an increase in the surcharge and effective depth of cut. The morphology and overall characteristics of these mesoscale structures (shear bands) do not change significantly with strain rate. The cutting force signatures were oscillatory and suggested cyclic material softening (dilation)-hardening (compaction) ahead of the tool, which is also reflected in the periodic repositioning of shear bands. The limit equilibrium-based model was adequate to predict the tool-cutting forces well, even with the significant variation in strain rates.