This paper presents an on-site experimental analysis of a high head hydro power plant and a storage pumping station, in an interconnected complex hydraulic scheme during simultaneous transient operation. The investigated hydropower site has a unique structure as the pumping station discharges the water into the hydropower plant penstock. The operation regimes were chosen for critical scenarios such as sudden load rejections of the turbines as well as start-ups and stops with different combinations of the hydraulic turbines and pumps operation. Several parameters were simultaneously measured such as the pumped water discharge, the pressure at the inlet pump section, at the outlet of the pumps and at the vane house of the hydraulic power plant surge tank. The results showed the dependence of the turbines and the pumps operation. Simultaneous operation of the turbines and the pumps is possible in safe conditions, without endangering the machines or the structures. Furthermore, simultaneous operation of the pumping station together with the hydropower plant increases the overall hydraulic efficiency of the site since shortening the discharge circuit of the pumps.