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Bereavement anniversary reactions, psychological, somatic, or behavioural responses triggered by dates associated with a significant loss, are frequently encountered in clinical practice but remain underexplored within psychodynamic frameworks. This systematic review aimed to identify and summarise published case studies describing anniversary reactions to bereavement and to assess whether these reports provide evidence relevant to psychoanalytic theory. A comprehensive search of five databases yielded 12 case studies reporting on 18 individual patients. These were reviewed through a descriptive and then psychoanalytic lens to identify patterns in symptoms, timing, type of loss, and contextual factors. Most involved sudden or traumatic deaths with mixed psychological and physical symptoms, often delayed or recurrent. A high proportion of cases showed anniversary reactions emerging long after the loss or recurring across multiple years. Our psychodynamic analysis of the material suggested an alignment of these anniversary reactions with established psychoanalytic concepts including, unconscious identification, in which aspects of the deceased are taken into the self and re-enacted at symbolic temporal markers, and the repetition compulsion, the drive to unconsciously re-live unresolved loss or trauma through symptom recurrence rather than symbolic mourning. This review highlights the clinical value of recognising anniversary reactions and suggests that deeper understanding of their psychodynamic underpinnings could enhance care for the bereaved.