This study explored the relationship between the morphological characteristics of the first tarsometatarsal ligaments and fibularis longus (FL) and the severity of articular cartilage degeneration in the first tarsometatarsal joint. Sixty legs from 30 cadavers were examined. The plantar, dorsal, and medial first tarsometatarsal ligaments were classified by fiber bundle number, and their morphological characteristics (fiber bundle length, width, thickness) were measured. The FL was categorized by its continuity with the plantar first tarsometatarsal ligament (PTML): Type A, connection with the PTML only on the first metatarsal; Type B, connection along the entire PTML; and Type C, no connection with the PTML. The severity of articular cartilage degeneration was assessed in four stages. No significant differences in cartilage degeneration among ligament types were found. Negative correlations were observed between the fiber bundle width and thickness of the PTML and the severity of cartilage degeneration. FL was classified as Type A in 68%, Type B in 27%, and Type C in 5% of feet. The fiber bundle thickness of the PTML in Type B was greater than in other types. Our findings suggest that smaller fiber bundle width and thickness in the PTML may be associated with severe cartilage degeneration. The FL had continuity with the PTML in 95% of feet and could enhance the mechanical strength of the PTML in Type B feet.