A print medium feeding device removes a second sheet from a print medium that is in a state in which a first sheet, the second sheet, a the third sheet are superposed, superposes the first sheet and the third sheet, and feeds the first sheet and the third sheet to a printing device. The print medium feeding device includes: a first roller configured to come into contact with the third sheet and to be driven to rotate by movement of the third sheet; a second roller configured to come into contact with the first sheet and to be driven to rotate by movement of the first sheet; a roll-up member disposed upstream of the first roller and configured to roll up the second sheet; and a transmission mechanism configured to transmit a rotational force of the first roller to the roll-up member.