Childlessness in late male adulthood is increasingly prevalent in rural China, indicating a need to understand the factors contributing to it. This group is often overlooked in gerontological and childlessness research. While existing studies have explored individual-level predictors of childlessness over the lifecourse and implications of broader societal conditions at the population level, little is known about how lifecourse and structural factors interact to shape pathways to childlessness. This study aims to investigate structural factors contributing to childlessness among older men in a rural area of northern China. It focuses on the life stories of 13 childless older men and the effects of history, timing and life-domain interdependencies, finding that some participants experienced intense disruptive life events or critical turning points – early-life care-giving responsibilities, disability or withdrawal from school – that altered their life trajectories. These events often intersected with structural factors, including unstable and low-paid employment, lack of social protection and prevailing social norms, which reinforced one another and jointly constrained prospects for marriage and parenthood. These trajectories unfolded within shifting policy contexts; institutional arrangements across different historical periods shaped and often produced disadvantages in the marriage market. This study advances theoretical understanding of the structural factors contributing to male childlessness by recognizing life trajectories, structural shifts and social relations as linked factors shaping cumulative disadvantage in union formation and childbearing. Its policy implications surround supporting individuals who intend to form families during critical life transitions and addressing the broader structural barriers that shape male childlessness in rural areas.