Chronic traumatic encephalopathy (CTE) results from repetitive brain injuries and is a common neurotraumatic sequela in contact sports. CTE is often accompanied by neuropsychiatric symptoms, which could escalate to suicidal ideation (SI) and suicidal behaviour (SB). Nevertheless, fairly limited emphasis about the association between suicidality and CTE exists in medical literature. Here, we report two cases of retired professional athletes in high contact sports (boxing and ice hockey) who have developed similar clinical trajectories characterized by progressive neuropsychiatric symptoms compatible with a CTE diagnosis and subsequent SB in its severe forms (medical serious suicide attempt (SA) and completed suicide). In addition to the description of outlining clinical, neuropsychological, neuroimaging, and differential diagnosis elements related to these cases, we also hypothesized some mechanisms that might augment the suicide risk in CTE. They include those related to neurobiological (neuroanatomic/neuroinflammatory) dysfunctions as well as those pertaining to psychiatry and psychosocial maladaptation to neurotraumas and retirement from professional competitive activity. Findings described here can provide clinical pictures to improve the identification of patients with CTE and also potential mechanistic insights to refine the knowledge of eventual severe SB development, which might enable its earlier prevention.