ABSTRACT While researchers have established that young men’s sporting friendships are often structured by violence, minimal intimacy, competition, and the degradation of all things feminine (Messner, 1992b), we know relatively little about sporting relationships between older men. Drawing on interviews with and ethnographic research of older male hockey players in two Canadian cities, this article finds that while those in late midlife (ages 54–71) continue to enact patterns of male relationships associated with younger men, those in later life (ages 71–82) break with these masculine patterns. Instead, their team relationships involve joking about themselves in the locker room (instead of mocking others) and an ethic of care. Many defined true or close friendships as those which extended beyond sport. These findings suggest that men’s alignment with the dominant sporting masculinity of the young is not static over the life course and may wane in certain arenas as men reach later life.