A cutting apparatus includes a holding conveying mechanism configured to convey a web using a holding surface, and a cutting mechanism configured to perform first cutting to cut the web conveyed while being held by the holding conveying mechanism along a crossing direction crossing a conveyance direction of the web and performing second cutting to cut the web along the crossing direction with a predetermined distance from the first cutting. The holding surface includes a main holding area configured to hold the web along the crossing direction between the first cutting and the second cutting, and an auxiliary holding area configured to hold the web by a holding power weaker than the holding power in the main holding area, at least in either upstream or downstream of the conveyance direction of the main holding area.
