Computational modelling of the in vivo mechanical response of various biological materials within the human organism, such as brain tissue, bone, arteries, ingested food, is an increasingly cost-effective design tool for bio-medical, bio-engineering and surgical applications. This study addresses the knowledge gap in simulating deformation-fracture during cutting in continua that lie in the transition between a soft solid and a complex fluid state. Hydrated food is one such system produced naturally after swallowing. We show that a viscoplastic-damage constitutive law calibrated through compression tests on hydrated biscuit particles, can be utilised in Eulerian Finite Element (FE) analysis to predict complex localised deformation-fracture material behaviour during cutting at two length scales with high fidelity. We demonstrate that in such materials a fracture term is not always necessary to predict ultimate separation and that the Eulerian FE analysis is a versatile approach based on which largely different material cutting behaviours can be modelled. Our study provides a platform for understanding and optimising processes involving ultra-soft materials which flow excessively and exhibit weak or strong cutting resistance.