In turbomachinery, the effect of cooling injection on the over-tip leakage (OTL) flow has been the focus. In the present work, the flow and heat transfer on the blade tip surfaces of two typical different tip structures including a flat tip and a squealer tip are investigated. The grid independence verification and turbulence model validation (including Shear Stress Transport k-ω model and Spalart-Allmaras model) are conducted. Numerical results are compared with the existing experimental results. It is found that there exists the shock wave near the corner of the pressure side, and a striped high-pressure coefficient region appears on the tip surface near the pressure side. The cooling injection could alter the range of high striped pressure coefficient region. The tip leakage vortex (TLV) was formed by the blending between the OTL flow and mainstream, causing a large aerodynamic penalty. In comparison, the flat tip shows a greater loss near the casing and the tip surface than the squealer tip. An interesting observation is that the coolant ejecting from the cooling jet hole bifurcates and then forms a counter-rotating vortex pair (CRVP) for both the flat tip and the squealer tip, which greatly changes the flow structures and heat transfer characteristics within the tip region. The branches of the CRVP cause the thermal stripes on the surfaces of blade tip and the suction side rim. The present results reveal the cooling injection has a strong effect on OTL flow and enlighten the design and optimization of blade tips.