A printing apparatus includes first and second supplying portions, a printer, and a winding unit. The first supplying portion can supply a recording medium on a conveyance route to the printer for first surface printing. The winding unit then rotates in a first direction to wind the printed recording medium. A wound recording medium edge is located at a specific location and then guided to a conveyance route opening portion if the wind direction is a second direction. After the edge is at the specific location, the recording medium is supplied through the opening portion to the printer for second surface printing. If the second supplying portion supplies the recording medium for first surface printing, then it supplies the medium for second surface printing. If a user sets a wound-in-advance recording medium to the second supplying portion, the second supplying portion supplies the set recording medium to the printer.