A printing system and a printing method are provided. The user terminal includes a print content processing unit and a sliding print content conversion unit, and the handheld printer includes an inkjet printing unit that performs inkjet printing at a predetermined inkjet width in a sliding direction when performing sliding print. The print content processing unit determines the number of sliding print motions and sequentially generates bitmaps corresponding to the respective sliding print motions based on the respective print content mode and the inkjet width, and generates bitmap format instructions corresponding to the respective bitmaps. The sliding print content conversion unit converts pixels in the bitmaps into binary data to form sliding print content. The handheld printer sequentially prints the respective sliding print content based on the respective bitmap format instructions and the print content mode.