Background Few studies have examined gender-specific pathways in the intergenerational transmission of internalizing and externalizing behaviors across three generations. Aim The current study considered both parental figures’ internalizing and externalizing symptom simultaneously and tested path models of the transmission of internalizing and externalizing symptoms from Generation 1 (G1) to Generation 2 (G2) and from G2 to Generation 3 (G3) by focusing on gender-specific pathways. Method The study used data from the Oregon Youth Study of 206 young men and two associated studies of their intimate partners (Couples Study) and children (Three-Generational Study) over 20 years. Results Findings indicated that, in general, mothers’ internalizing behaviour showed robust influence on offspring’s internalizing symptoms across three generations, regardless of gender of the child. G2 men’s externalizing behaviour was further predicted by G1 mothers’ internalizing as well as externalizing behaviour, albeit the latter was only marginally significant. G3 girls’ internalizing and externalizing behaviour was predicted by their fathers’ corresponding behaviour. Overall, fathers’ influence on their sons was limited. Conclusion The findings shed important light on potential gender-specific mechanisms of intergenerational transmission of internalizing and externalizing behaviour.