We report theoretical, numerical, and experimental studies of cascaded phase matching in fiber frequency combs and show how this mechanism is directly connected to the dynamics of supercontinuum generation. In particular, linking cascaded four-wave mixing with direct higher-order nonlinear processes allows us to derive a simple phase matching condition that governs nonlinear symmetry breaking in the presence of higher-order dispersion. We discuss how this mechanism provides a physical interpretation of soliton-induced Cherenkov radiation and associated spectral recoil in terms of phase-matched frequency mixing pumped by bichromatic pump pairs in the soliton spectrum. Theoretical and numerical predictions are confirmed via experiments using both quasicontinuous wave and picosecond pulse excitation.