Decompression sickness (DCS), traditionally associated with SCUBA diving, increasingly occurs in breath-hold diving, particularly during repetitive shallow or deep dive profiles. This comprehensive review synthesizes 85 records documenting 244+ cases across 75 years, including historical Taravana syndrome in Polynesian pearl divers and cases among Japanese Ama, Korean Haenyeo, recreational freedivers, instructors, and spear fishers. Unlike SCUBA-related DCS, breath-hold DCS predominantly manifests as cerebral symptoms that can mimic stroke or transient ischemic attack, often presenting in young, healthy individuals. Key risk factors include inadequate surface intervals during repetitive shallow dives, deep dives exceeding 40 m, rapid ascent rates, and individual physiological factors including patent foramen ovale. Despite growing freediving popularity with an estimated one million participants globally, DCS remains underrecognized and underreported. Early recognition is critical, requiring high clinical suspicion in divers presenting with neurological symptoms. Immediate high-flow oxygen and urgent hyperbaric oxygen therapy remain essential treatments. This review emphasizes the need for enhanced education among both divers and medical professionals to improve prevention, recognition, and management of this potentially devastating condition.