Background: There continues to be controversy regarding the simultaneous encouragement of both breastfeeding and immediate postpartum contraception. Research Aim: To explore postpartum women’s perspectives about breastfeeding and their breastfeeding behaviors, while using one of three different hormonally systemic contraceptive methods immediately postpartum over a 6 month period of time. Methods: This was a retrospective, longitudinal, three group comparative, secondary analysis of a prospective cohort study ( N = 471) of immediate postpartum contraception. Breastfeeding, for this study, was defined as providing any human milk to the infant. Participants who chose one of three different hormonally systemic forms of contraception immediately postpartum (a long-acting hormonal reversible contraceptive ( n = 200), depot medroxyprogesterone acetate 150 mg ( n = 98), or a non-hormonal method ( n = 173)) were compared at hospital discharge, 6 weeks, 3 months, and 6 months postpartum. The primary outcome was any breastfeeding at 6 months. Secondary outcomes included any and exclusive breastfeeding, concerns about breastfeeding while using contraception, and reasons for breastfeeding discontinuation. Results: There was no significant difference in the rate of any breastfeeding between the two hormonal and the non-hormonal contraceptive groups at 6 months postpartum (long-acting hormonal 20.1%, non-hormonal 21.7%, depot medroxyprogesterone acetate 13.9%, p = .77, 0.28, respectively). The number of participants who reported stopping breastfeeding due to decreased milk supply was not significantly different between any groups at all time points (total number who discontinued at 6 months postpartum was long-acting hormonal 24.7%, non-hormonal 25.1%, depot medroxyprogesterone acetate 19.3%, p = .30). Conclusions: Breastfeeding perspectives and behavioral outcomes over the first 6 months postpartum were not influenced by participants chosen form of immediate postpartum contraception.