Maternal depression is an established risk factor for child conduct problems, but relatively few studies have tested whether children's behavioral problems exacerbate mothers' depression or whether other child behavioral characteristics (e.g., self-regulation) may mediate bidirectional effects between maternal depression and child disruptive behavior. This longitudinal study examined the parallel growth of maternal depressive symptoms and child oppositional behavior from ages 2 to 5; the magnitude and timing of their bidirectional effects; and whether child inhibitory control, a temperament-based self-regulatory mechanism, mediated effects between maternal depression and child oppositionality. A randomized control trial of 731 at-risk families assessed children annually from ages 2 to 5. Transactional models demonstrated positive and bidirectional associations between mothers' depressive symptoms and children's oppositional behavior from ages 2 to 3, with a less consistent pattern of reciprocal relations up to age 5. Mediation of indirect mother-child effects and child evocative effects depended on the rater of children's inhibitory control. Findings are discussed in regard to how child evocative effects and self-regulatory mechanisms may clarify the transmission of psychopathology within families.