The presented research is a part of widely research of the nonlinear dynamic behaviour of rolling bearings, which are the parts of all rotating assemblies and machinery. In accordance with the state-of-the-art requirements for the advanced mechanical design and industrial digitalization, the large experiments and research are performed and the new mathematical model of the dynamic behaviour of rolling bearings with damages is developed. The results obtained for a particular type of deep groove ball bearings are presented, and the possible further research and implementation of the obtained model in digitalized self-monitoring systems is discussed.