This study evaluated relationships between maternal perceptions of infant sleep, settling and crying patterns and breastfeeding. A prospective observational study of 91 mothers of healthy, term infants was conducted with follow ups over 9 months after discharge from a Western Australian maternity hospital. Feeding information, sleep, settle and cry behaviours, maternal bother at infant behaviours and confidence were measured using the Sleep and Settle Questionnaire. Breastfeeding confidence was measured using the Breastfeeding Self-Efficacy Scale—Short Form. Questionnaires were administered at 2 and 6 weeks, 3, 6 and 9 months. Linear mixed models were used to assess associations between maternal bother, feeding method and infant characteristics. The feeding method was not associated with maternal bother, and cessation of breastfeeding did not result in a change in bother scores (p = 0.34). Duration of infant crying in the day, evening and night, frequency of night waking and duration of settling to sleep in the day were associated with increased bother scores. Higher breastfeeding self-efficacy and maternal confidence were associated with lower bother scores (both p < 0.01). Maternal bother is associated with infant behaviours that require parental input, but not breastfeeding status. Resources that address parental expectations regarding infant sleep while providing strategies to support maternal wellbeing and breastfeeding are needed.