This paper presents the characteristics of the different stages in the evolution of the wake of a circular cylinder rolling without slipping along a wall at constant speed, acquired through numerical stability analysis and two-and three-dimensional numerical simulations. Reynolds numbers between 30 and 300 are considered. Of importance in this study is the transition to three-dimensionality from the underlying two-dimensional periodic flow and, in particular, the way that the associated transitions influence the fluid forces exerted on the cylinder, and the development and the structure of the wake. It is found that the steady two-dimensional flow becomes unstable to threedimensional perturbations at Re c,3D = 37, and that the transition to unsteady twodimensional flow -or periodic vortex shedding -occurs at Re c,2D = 88, thus validating and refining the results of Stewart et al. (2010). The main focus here is for Reynolds numbers beyond the transition to unsteady flow at Re c,2D = 88. From impulsive start up, the wake almost immediately undergoes transition to a periodic two-dimensional wake state, which, in turn, is three-dimensionally unstable. Thus, the previous threedimensional stability analysis based on the two-dimensional steady flow provides only an element of the full story. Floquet analysis based on the periodic two-dimensional flow was undertaken and new three-dimensional instability modes were revealed. The results suggest that an impulsively started cylinder rolling along a surface at constant velocity for Re 90 will result in the rapid development of a periodic two-dimensional wake that will be maintained for a considerable time prior to the wake undergoing threedimensional transition. Of interest, the mean lift and drag coefficients obtained from full three-dimensional simulations match predictions from two-dimensional simulations to within a few percent.