Firm, crispy and crunchy texture is an important factor of plant-based foods. Pre- and post-failure processes of cucumber cultivars were examined to explore the mechanical properties that determine cultivar-specific crispy and crunchy texture. Spatial distribution of mechanical properties, which can be a very important characteristic in relation to food textural quality, was visualized and characterized for the mechanically complex and heterogeneous structure of cucumber fruits. A multiple-point sheet sensor system, which shows time series of spatial stress distribution on a sample, successively demonstrated the characteristics of the stress distribution in each tissue of cucumbers and its differences among cultivars during the prefailure process of compression tests. For the postfailure process, it was confirmed how fractures occur, as either a major global fracture event or a number of sequential small local fractures. The two-dimensional information about postfailure events enabled us to relate the structural fracture phenomenon to the force-strain property of each cultivar. This technique is applicable to other food materials to explore the relationships among their mechanical properties, structure, and texture.