- Background: Low birthweight and preeclampsia are both adverse pregnancy and delivery outcomes, with possible influence on future health status. Previous studies have shown that intergenerational factors may be important prognostic information in evaluating women prior to or after conception. Our objective was to evaluate the role of intergenerational factors on the incidence of preeclampsia and low birthweight (LBW). Methods: A retrospective population-based study was conducted. Perinatal information was gathered from 2311 familial triads, comprising mothers (F1), daughters (F2), and children (F3). All births occurred in a tertiary medical center between 1991 and 2013. A multivariate generalized estimating equation logistic regression model analysis was used to study the association between LBW and preeclampsia across generations while controlling for confounders and for clusters of families in the database. Results: A total of 1490 in F1, 1616 in F2, and 2311 in F3 were included. LBW in mothers (F2), adjusted for possible confounders, was found to be a significant predictor for LBW in offspring (OR = 1.6, 95% CI 1.02–2.6, p = 0.043). Likewise, preeclampsia was also noted as a significant intergenerational factor following adjustments for possible confounders (OR = 2.9, 95% CI 1.4–5.8, p = 0.004). Conclusions: Maternal LBW and preeclampsia are both independent risk factors for recurrence in the next generation.