Minimizing numerical dissipation without compromising the robust shock-capturing attributes remains an outstanding challenge in the design of numerical methods for high-speed compressible flows. The conflicting requirements of low and high numerical dissipation for accurate resolution of discontinuous and smooth flow features, respectively, are the principal reason behind this challenge. In this work we pursue a recently proposed novel strategy of combining adaptive mesh redistribution with conservative high-order shock-capturing finite-volume discretization methodology to overcome this challenge. In essence, we perform high-order finite-volume WENO (weighted essentially non oscillatory) reconstruction on a continuously moving grid the nodes of which are repositioned adaptively in such a way that maximum spatial resolution is achieved in regions associated with sharpest flow gradients. Moreover, to reduce computational expense, the finite-volume WENO discretization strategy is combined with the midpoint quadrature so that only one reconstruction along each intercool location is necessary. To estimate a monotone upwind flux, a rotated HLLC (Harten-Lax-vanLeer-contact resolving) Riemann solver is employed at each intercool location with the state variables estimated from the high-order WENO reconstruction procedure. The effectiveness of this adaptive high-order discretization methodology is assessed on the well-known double Mach reflection test case for reconstruction orders ranging from five to eleven. We find that the resolution of the intricate flow features such as the wall-jet improves progressively with the reconstruction order, which is indicative of the reduced dissipation level of the adaptive high-order WENO discretization. The adaptive discretization methodology is applied to simulate a flow configuration consisting of a Mach 3 supersonic jet injected in a Mach 2 supersonic crossflow of similar ideal gas. It is found that the flow characteristics and especially features that are formed as a result of the Kelvin-Helmholtz instability are strongly influenced by the reconstruction order. The influence of the jet inclination angle on the overall flow features is analyzed.