The tip region of transonic turbine blades (exit Mach number of 0.95) exhibits complex flow characteristics with the coexistence of multiple shock wave systems and multiscale vortices. Based on a validated detached Eddy simulation method, unsteady flow features such as the spatial-temporal dynamic evolution of tip leakage vortices (TLV) and the periodic buffet/oscillation of shock trains inside the tip gap are revealed and discussed systematically under different incidence angles (i) and heights of tip clearance. Moreover, the distinction of tip flow structures between the subsonic and transonic conditions is also manifested. Results indicate that the wandering behavior of the TLV is influenced by both the swirling strength of the vortex itself and the interaction of adjacent secondary vortices. The TLV under a tip gap of 5% blade height (h) exhibits “binary and bimodal” wandering characteristics both along the pitchwise and spanwise direction, whereas under the 1%h case, only the pitchwise wandering is prominent. The dominant characteristic frequency of the TLV wandering under different conditions falls within the spectrum range of 2.2–2.4 kHz. As for the shock trains inside the tip clearance (τ), coherently movement back and forth along the pitchwise direction with varying amplitudes can be observed, where the magnitude within the τ=1%h exceeds that observed in the τ=5%h, depending on the intensity of the shock waves. Notably, significant shock wave oscillations are present throughout the range of the chord length (c) within the τ=1%h, whereas within the tip gap of 5%h, shock wave systems exhibit more pronounced oscillations predominantly near the trailing edge.