Although identified in the definition of leisure constraints, leisure enjoyment has been rarely studied as an outcome of constraints and constraint negotiation. The purpose of this paper is, therefore, to examine the associations among leisure constraints, constraint negotiation, and enjoyment, within the context of leisure-time physical activity (LTPA). Cross-sectional online survey data from 618 Japanese and Euro-Canadian adults were used. Regression results suggested that across different levels of LTPA, enjoyment was negatively associated with constraints and positively with constraint negotiation. Follow-up regression analyses at sub-category level identified specific types of leisure constraints and negotiation strategies particularly pertinent to enjoyment. We conclude that leisure enjoyment is a direct outcome of constraints and constraint negotiation, which supports the call to extend the leisure constraints theory beyond participation as the outcome. Moreover, we suggest that facilitating leisure enjoyment requires awareness of different types of constraints and negotiation strategies depending on activity contexts.