This study investigates numerical analysis of the oblique shock/boundary-layer interaction (OSBLI) in a Mach 1.7 flow with a unit Reynolds number of 35 million. Two methods of simulations are performed and compared with an experiment. While two different delayed detached-eddy simulations (DDES) are performed to simulate the fullspan geometry, a wall-modeled large-eddy simulation (WM-LES) is carried out to study the physics near the mid-span area. In the experiment, the boundary layer is tripped at the leading edge of the flat plate to ensure fully turbulent boundary layer at the interaction zone. The tripping device in the WM-LES computations was simulated by artificial blowing and suction, while in the DDES simulation turbulence is generated by a Reynolds-Averaged Navier-Stokes (RANS) model and its intensity is adjusted to match the experimental one. Challenges to simulate this test case as well as comparison between the two numerical studies with the experimental results a re highlighted in this paper.