We report the experimental observation of vortex leapfrogging in a two-dimensional fluid of light. By imprinting two vortex–antivortex pairs and tracking their real-time evolution through phase-resolved imaging, we observe a dynamics that is accurately described by a point-vortex model with an outward background flow. By precisely controlling the initial vortex separation, we identify configurations in which leapfrogging breaks down and observe two different dissipation mechanisms. The first originates from phase slip events occurring at large injected velocities. The second arises when the injection of multi-charged vortices leads to the formation of a quasi one-dimensional dispersive shock wave which acts as a continuous source of phase slippage.