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Background/Objectives: Maternal postpartum depressive symptoms and the COVID-19 pandemic have both been identified as potential risk factors for socioemotional difficulties in children. This study aimed to assess behavioral outcomes in young children born to mothers previously screened for postpartum depressive symptoms, comparing cohorts evaluated during and after the pandemic using the Child Behavior Checklist (CBCL 1½-5). Methods: An observational follow-up cohort study was conducted on 52 mother-child dyads derived from a previously established maternal cohort screened with the Edinburgh Postnatal Depression Scale (EPDS). Two cohorts were defined according to the child's birth period: during-pandemic (January-April 2022) and post-pandemic (October-November 2023) groups. Behavioral outcomes were assessed using CBCL 1½-5. Group differences were tested using parametric or non-parametric methods for continuous variables and χ2 or Fisher's exact tests for categorical variables. Exploratory regression models and sensitivity analyses were also performed. Results: Children assessed in the post-pandemic cohort showed a lower prevalence of non-normal internalizing scores than those assessed in the during-pandemic cohort, whereas externalizing outcomes and Total Problems did not significantly differ between groups. In exploratory models, a child's age showed a near-significant association with internalizing outcomes, suggesting that developmental stage at assessment may have contributed to the observed cohort difference. Maternal SARS-CoV-2 infection at delivery was not associated with children's behavioral outcomes. Conclusions: These findings suggest a possible difference in internalizing behavioral profiles between children assessed in during-pandemic and post-pandemic cohorts. However, this pattern should be interpreted cautiously because the cohorts differed substantially in age at follow-up, and age-related factors may have affected symptom detectability. Continued longitudinal follow-up will be important to clarify whether the observed differences persist over time.