The purpose of this paper is designing a head control system capable of adapting to passive side-slipping. The environments in which snake-like robots are expected to be utilized generally have ground surface conditions with nonuniform frictional coefficients. In such conditions, the passive wheels of the snake-like robot have a chance of side-slipping. To locomote the snake-like robot dexterously, a control system which adapts to such side-slipping is desired. There are two key points to realizing such a system: First, a dynamic model capable of representing the passive side-slipping must be formulated. A solution for the first key point is to develop a switching dynamic model for the snake-like robot, which switches depending on the occurrence of the side-slipping, by utilizing a projection method. The second key point is to adapt the control system’s behavior to side-slipping. An idea for such a solution is to include the side-slipping velocity in the weighting matrices. An algorithm to estimate the occurrence of side-slipping and the particular side-slipping link is constructed, to formulate the dynamic model depending on the actual side-slipping situation. The effectiveness of the designed Luenberger observer and the head control system for side-slipping adaptation is verified through numerical simulation.