The clinical records of five men who had sexually assaulted women aged 60 or over were compared to the records of seven men who had sexually assaulted younger victims. Details of childhood adjustment, psychiatric and criminal histories, psychiatric diagnosis, psychological assessment findings, and offence characteristics were examined to determine psychological and social factors specifically associated with the sexual assault of older women. The findings suggest that when victims are older women, the sexual assault is likely to be particularly brutal and largely motivated by anger, a need for power, or sadistic intent. Further, the gratuitous violence involved in the offences and clinical evidence of psychotic features, suggest more severe psychopathological processes in men who sexually assault older women than in those who assault younger victims. Implications for theory and clinical practice are discussed.