A bubble’s motion is strongly influenced by the boundaries of tip structures, which correspond to the bubble’s size. In the present study, the dynamic behaviors of a cavitation bubble near a conical tip structure are investigated experimentally and numerically. A series of experiments were carried out to analyze the bubble’s shape at different relative cone distances quantitatively. Due to the crucial influence of the phase change on the cavitation bubble’s dynamics over multiple cycles, a compressible two-phase model taking into account the phase change and heat transfer implemented in OpenFOAM was employed in this study. The simulation results regarding the bubble’s radius and shape were validated with corresponding experimental photos, and a good agreement was achieved. The bubble’s primary physical features (e.g., shock waves, liquid jets, high-pressure zones) were well reproduced, which helps us understand the underlying mechanisms. Meanwhile, the latent damage was quantified by the pressure load at the cone apex. The effects of the relative distance γ and cone angle θ on the maximum temperature, pressure peaks, and bubble position are discussed and summarized. The results show that the pressure peaks during the bubble’s collapse increase with the decrease in γ. For a larger γ, the first minimum bubble radius increases while the maximum temperature decreases as θ increases; the pressure peak at the second final collapse is first less than that at the first final collapse and then much greater than that one. For a smaller γ, the pressure peaks at different θ values do not vary very much.