Background: Little empirical research examines relationships among delivery mode, other childbirth-related factors, maternal characteristics, and child psychosocial development. Objective: The aim of this study is to explore the developmental trajectories of toddlers' emotional and behavioral problems and the predictive role of psycho-social, childbirth, and maternal characteristics. Method: Participants were 258 mothers and their children who took part in a longitudinal study from birth till the age of 30 months. Self-report instruments were used for the assessment of mothers' infant rearing attitudes, the quality of relationship with the partner, maternal emotional distress, and maternal self-efficacy. The Child Behavior Checklist (1½-5) was used for the assessment of children's behavioral and emotional problems. Results: Latent class analysis for emotional and behavioral problems ended in 3-class solutions. In regard to emotional problems, 83% of children were classified as having a stable low, 11% an increasing, and 6% a decreasing level of emotional problems. In regard to behavioral problems, 86% of children showed a stable low, 5% an increasing, and 9% a stable high level of behavioral problems. Children's gender in combination with maternal education and maternal infant rearing attitudes predict children's membership in the increasing and decreasing emotional problem classes. Children's gender and maternal age in combination with emergency caesarean section, the quality of the relationship with the partner, and maternal self-efficacy explain children's membership in the classes of high and increasing behavioral problems. Conclusions: A combination of such factors as emergency caesarean section, child's gender, maternal age and level of education, maternal infant rearing attitudes, maternal self-efficacy, and inter-parental relationships predict developmental trajectories of emotional and behavioral problems in toddlers.