This study explored the link between vitamin D status and frequency of skin infections, inflammation, and injury in college wrestlers during an academic year. Methods: Serum 25-hydroxyvitamin D (25(OH)D) (n = 19), plasma cytokine (TNF-α, IL-6, IL-10) (n = 18) concentrations, and body weight/composition were measured and injury/illness/skin infection data were collected in fall, winter, and spring. Results: In the fall, 74% of wrestlers had vitamin D concentrations <32 ng/mL which increased to 94% in winter and spring. Wrestlers lost an average of 3.4 ± 3.9 kg (p < 0.001) during the season with corresponding decreases in fat mass and increases in lean mass (p < 0.01). An inverse association between 25(OH)D concentrations and total body mass and body fat percentage was observed at all-time points (p < 0.01). Concentrations of cytokines were highly variable among individuals and did not change across time (p > 0.05). Correlations between vitamin D status, cytokines, or frequency of illness, injury, or skin infections were not observed. Conclusions: A high prevalence of vitamin D insufficiency (<32 ng/mL) and deficiency (<20 ng/mL) was observed in wrestlers and was associated with higher adiposity. It remains unclear if higher vitamin D status would reduce injury, illness, and skin infection risk.