The present study had three objectives. The first objective was to examine trajectories of gambling frequency and problems from mid-adolescence to adulthood in a Canadian population-representative cohort of 2000 boys and girls, part of an ongoing longitudinal study since kindergarten. Trajectories were based on self-report at three times of assessment: ages 15–16, 22–23, and 29–30. The second objective of the present study was to investigate childhood risk factors associated with computed trajectories of gambling frequency and problems. Finally, the third objective was to assess the consequences of following different trajectories of gambling behaviours for 29–30 years-old adults, their family and children. Results are discussed based on a developmental, intergenerational perspective on gambling behaviours and problems.