A cutting apparatus includes a cutter, a controller and a memory configured to store instructions. The instructions instruct the controller to execute steps including arranging patterns including peripheral lines including sequential line segments. The pattern arrangement includes arranging the patterns so that the line segments of adjacent patterns overlap each other. The instructions further include identifying the overlapping line segments, generating data representing a line including the identified overlapping line segments, designating the patterns including the overlapping line segments as a pattern group and extracting parallel line segments from the line segments forming the pattern group, grouping the extracted parallel line segments into line segments parallel to each other and denoting an identical cutting direction, determining a cutting order of the line segments composing the pattern group of the patterns including the overlapping line segments and generating a signal based on the generated data and the determined cutting order.