The cavity expansion theory is commonly employed to predict the grouting pressure and cone penetration resistance. However, existing theoretical solutions for cohesive-frictional soils with dilation fail to simultaneously consider both the elastic deformation in the plastic zone and strain-softening behaviour of soils. To address this limitation, a similarity solution was derived for the expansion of spherical cavities from a zero initial radius with an initial confining pressure in strain-softening Mohr–Coulomb materials. The results demonstrate good agreement with previous theories, predicting an ultimate pressure higher than that obtained by neglecting elastic deformation in the plastic zone but lower than that calculated by neglecting softening characteristics. Moreover, several influential factors affecting the radius of the plastic zone and ultimate pressure were meticulously examined. On-site cone penetration test data and the theoretical results showed notable agreement. This indicates that the proposed solution exhibits a better conformance with the field data than do the previous solutions.