Boxing is a violent sport in which every participant accepts the risk of brain damage or death. This sport has been linked to acute neurological injury and chronic brain damage. The most common life-threatening injury encountered by its participants is subdural hematoma (SDH), and the most feared consequence of chronic insult to the nervous system is dementia pugilistica, or punch drunkenness. Although advances in imaging and neuropsychological testing have improved our ability to diagnose these injuries, the unprecedented sensitivity and wide availability of these modalities have increased the detection of mild cognitive impairment and small, asymptomatic imaging abnormalities. The question has thus been raised as to where on the spectrum of these injuries an athlete should be permanently banned from the sport. In this report the authors describe six boxers who were evaluated for SDH sustained during participation in the sport, and who experienced remarkably different outcomes. Their presentations, clinical courses, and boxing careers are detailed. The athletes ranged in age from 24 to 55 years at the time of injury. Two were female and four were male; half of them were amateurs and half were professionals. Treatments ranged from observation only to decompressive craniectomy. Two of the athletes were allowed to participate in the sport after their injury (one following a lengthy legal battle), with no known sequelae. One boxer died within 48 hours of her injury and at least two suffered permanent neurological deficits. In a third, dementia pugilistica was diagnosed 40 years later, and the man died while institutionalized.