Dimples are shallow surface indentations that have been recently considered as a passive viscous drag reducing technique for turbulent boundary layers. Studies so far were limited to incompressible low-Re flows and display little consensus on whether dimples can actually produce net improvements in total drag. Conversely, dimple geometry can be regarded as the inverse of transonic bumps, a matured wave drag reduction. In light of this, this thesis sets off to analyse the flow structures that arise over dimples at transonic speeds provide, serving as an initial assessment of their wave drag reducing potential. A transonic flow was reproduced experimentally using an asymmetric nozzle. Then, the performance of five dimple designs was evaluated against the criteria adopted for transonic bumps. Measurements included Schlieren, surface pressure and PIV. Results reveal that small spherical dents seem to produce spanwise excitations that subdue the detrimental effects of expansion fans formed at their edges, and ultimately allow for a higher momentum retention across the interaction.