In this study, oblique-shock/bow-shock interference is theoretically and numerically studied with two incident shock waves. The transition criteria between the two modes of multiple shock–shock interference, i.e., the concomitant-jet (CJ) and dual-jet (DJ) modes, are given. The oblique shock relationship and shock polar analysis are utilized to obtain the analytical solution of the transition condition. The theoretical results indicate the existence of a dual solution interval (DSI) that widens with increasing Mach number and narrows with increasing deflection angle induced by the first incident shock wave. The DSI obtained by numerical simulation is considerably narrower than that theoretically predicted due to the advanced CJ→DJ and DJ→CJ transitions. The analysis reveals that the transitions are advanced due to the downstream disturbance and secondary waves in the flow field.