Aims This work aimed to study consequences of medical interventions in connection with birth on infant pre-feeding and feeding behaviors and on maternal oxytocin levels in connection with a breastfeed 2 days later. Materials and Methods Mothers and their full-term newborns (n = 41) were videotaped during a breastfeed 2 days after birth. Duration and quality of rooting [Infant Breastfeeding Assessment Tool (IBFAT)] were assessed. Maternal blood samples were collected, oxytocin levels were analyzed, and mean oxytocin level and variance were calculated. Data on medical interventions during birth, number of breastfeedings, and infant weight loss since birth were recorded. Data were analyzed using logistic regression models. Results The duration of infant rooting was significantly shorter when the mother had received epidural analgesia. The shorter the duration of infant rooting, the more often infants had breastfed and the greater was the infant weight loss since birth. Mothers with epidural analgesia with oxytocin had the lowest oxytocin mean levels in connection with a breastfeed. Oxytocin variance correlated positively with quality of rooting and correlated negatively with infant weight loss. In the control group alone, we found similar patterns of associations with oxytocin levels. Conclusion Epidural analgesia and epidural analgesia with oxytocin infusion in connection with birth negatively influenced infant rooting behavior and maternal mean oxytocin levels, respectively. Oxytocin infusion alone was without effect. The data also suggest that infants who suck well stimulate oxytocin release more efficiently, as expressed by a high oxytocin variance, leading to a better stimulation of milk production and consequently to a reduced infant weight loss 2 days after birth.