The implementation of artificial ventilation schemes is necessary when respiration fails. One approach involves the application of high frequency oscillatory ventilation (HFOV) to the respiratory system. Oscillatory airflow in the upper bronchial tree can be characterized by Reynolds numbers as high as 10(4), hence, the flow presents turbulent features. In this study, transitional and turbulent flow within an asymmetric bifurcating model of the upper airway during HFOV are studied using large eddy simulation (LES) methods. The flow, characterized by a peak Reynolds number of 8132, is analysed using a validated LES model of a three-dimensional branching geometry. The pressures, velocities, and vorticity within the flow are presented and compared with prior models for branching flow systems. The results demonstrate how pendelluft occurs at asymmetric branches within the respiratory system. These results may be useful in optimising treatments using HFOV methods.