We have conducted high-pressure measurements on the CuCr₂O₄ and CuCr₂Se₄ spinels to unravel the structural systematics of these materials under compression. Our studies have revealed diverse structural behavior in these two compounds. In particular, CuCr₂O₄ retains its ambient-pressure I4₁/amd structure up to 50 GPa. Close inspection of the lattice and interatomic parameters reveals a compressibility change near 23 GPa, which is accompanied by an expansion of the apical Cr-O bond distances. We speculate that an outer Cr³⁺ 3d orbital reorientation might be at play in this system, manifesting as the change in compressibility at that pressure point. On the other hand, CuCr₂Se₄ undergoes a structural transformation from the starting Fd3̄m phase toward a monoclinic structure initiated at ∼8 GPa and completed at ∼20 GPa. This high-pressure behavior resembles that of ZnCr₂Se₄, and it appears that, unlike similar chalcogenide Cr spinels, steric effects take a leading role in this pressure-induced Fd3̄m → monoclinic transition. Close comparison of our results with the reported literature yields significant insights behind the pressure-induced structural systematics of this important family of materials, thus both allowing for the careful manipulation of the structural/physical properties of these systems by strain and promoting our understanding of similar pressure-induced effects in relevant systems.