Background/Objectives: Chronic pain impacts approximately 18% of the Spanish population, with low levels of vitamin D prevalent in over 80% of individuals over 65. Given vitamin D’s critical role in pain modulation, its deficiency may be significantly linked to chronic musculoskeletal pain, though existing research offers mixed results. Methods: This systematic review followed PRISMA guidelines, examining studies from PubMed, Cochrane, and PEDRO databases from 1990 onwards that investigated the relationship between vitamin D levels and chronic musculoskeletal pain. Results: A total of 30 studies met the inclusion criteria set by the NHLBI’s quality standards. The results are inconclusive regarding the direct relationship between vitamin D levels and chronic musculoskeletal pain due to evidence heterogeneity. However, there appears to be an inverse relationship between vitamin D levels and the intensity of pain. Conclusions: While the association between vitamin D levels and chronic musculoskeletal pain remains uncertain, the inverse correlation with pain intensity suggests a potential therapeutic role of vitamin D supplementation in pain management. Further research is needed to substantiate these findings and refine intervention strategies.