A cutting apparatus 1 includes a holding conveying mechanism 30 configured to convey a web W using a holding surface 32A, and a cutting mechanism 20 configured to perform first cutting to cut the web W conveyed while being held by the holding conveying mechanism 30 along a crossing direction CD crossing a conveyance direction MD of the web W and performing second cutting to cut the web along the crossing direction CD with a predetermined distance from the first cutting. The holding surface 32A includes a main holding area 301 configured to hold the web along the crossing direction CD between the first cutting and the second cutting, and an auxiliary holding area 302 configured to hold the web W 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 MD of the main holding area.
