The squeal phenomenon is often generated in bicycle disc brakes. This paper deals analytically with the generation mechanism and the criterion of whether or not the squeal occurs. According to the experimental studies, it has been made clear that the squeal is mainly in-plane vibration in the direction of disc surface with the frequency about 1kHz caused by frictional characteristics with negative slope with respect to the relative velocity. An analytical model of the bicycle disc brake system has been devised to confirm the experimental results, in which a coupled in-plane and out-of-plane vibrating system is composed of the disc, hub, caliper and spokes. The resulting frequency of squeal and the unstable vibration modes of the disc and spokes from the analytical model agreed well with the experimental results.