Gross features of disc degeneration (DD) that are associated with back pain include tears in the anulus fibrosus, structural changes of the endplates, and a collapse of the anulus. The aim of this study is the detailed visualization and microstructural characterization of DD using microcomputed tomography (μCT) and a dedicated image post-processing pipeline. In detail, we investigate a cadaveric spine that shows both types of DD between L1 and L2 and between L2 and L3, respectively. The lumbar spine was obtained from a male donor aged 74 years. The complete specimen was scanned using μCT with an isometric voxel size of 93 μm. Subsequently, regions of interest (ROI) were prepared featuring each complete intervertebral disc including the adjacent endplates. ROIs were then additionally scanned with a voxel size of 35 μm and by means of magnetic resonance imaging. The collapsed endplate of the superior L2 showed explicit signs of an endplate-driven degeneration, including bony endplate failures. In contrast, the intervertebral disc between L2 and L3 showed indications of an annulus-driven DD including severe disc height loss and concentric tears. Using μCT we were able to visualize and quantify bone and cartilage features in DD. We showed that in both cases a suite of structural changes accompanies cartilage degeneration, including microstructural bony adaptions to counteract changes in the biomechanical loading regimen.