The present disclosure provides advantageous breastfeeding devices and/or assemblies. More particularly, the present disclosure provides advantageous vacuum assisted breastfeeding devices/assemblies, and related methods of use. The present disclosure provides assemblies/devices to assist mothers in breastfeeding infants. The advantageous assemblies/devices of the present disclosure can provide feeding assistance and improved breastfeeding rates to infants (e.g., premature infants) while they are being held close to the mother and feeding. Premature infants, and full-term infants with developmental delays, transient breastfeeding problems, and or cleft lip and palate can get several benefits from the assemblies/devices of the present disclosure.