Helical deep hole drilling is a process frequently used in industrial applications to produce bores with a large length to diameter ratio. For better cooling and lubrication, the deep drilling oil is fed directly into the bore hole via two internal cooling channels. Due to the inaccessibility of the cutting area, experimental investigations that provide information on the actual machining and cooling behavior are difficult to carry out. In this paper, the distribution of the deep drilling oil is investigated both experimentally and simulatively and the results are evaluated. For the Computational Fluid Dynamics (CFD) simulation, two different turbulence models, i.e. the RANS k-ω-SST and hybrid SAS-SST model, are used and compared. Thereby, the actual used deep drilling oil is modelled instead of using fluid dynamic parameters of water, as is often the case. With the hybrid SAS-SST model, the flow could be analyzed much better than with the RANS k-ω-SST model and thus the processes that take place during helical deep drilling could be simulated with realistic details. Both the experimental and the simulative results show that the deep drilling oil movement is almost exclusively generated by the tool rotation. At the tool’s cutting edges and in the flute, the flow velocity drops to zero for the most part, so that no efficient cooling and lubrication could take place there. In addition, cavitation bubbles form and implode, concluding in the assumption that the process heat is not adequately dissipated and the removal of chips is adversely affected, which in turn can affect the service life of the tool and the bore quality. The carried out investigations show that the application of CFD simulation is an important research instrument in machining technology and that there is still great potential in the area of tool and process optimization.