To provide a printing apparatus and a printing method that can prevent an adhesive sheet and a release sheet from shifting in position when temporarily stuck again.

A printing apparatus 1 includes: paying out means 2 of paying out a web R having a belt-like adhesive sheet S temporary stuck on one surface of a belt-like release sheet RL; bypassing means 3 of temporarily releasing and bypassing the release sheet RL from the adhesive sheet S of the web R; printing means 4 of printing on at least one of surfaces of one or the other of an adhesive layer AD of the adhesive sheet S exposed by bypassing the release sheet RL and the release sheet RL bypassed from the adhesive sheet S; temporary sticking means 6 of temporarily sticking the adhesive sheet S on the bypassed release sheet RL again; second positioning means 8 of positioning with respect to predetermined positions, relative positions of the release sheet RL and adhesive sheet S in an in-matching-plane direction between the release sheet RL and adhesive sheet S in the temporary re-sticking, and in a positioning direction orthogonal to the paying out direction of the sheets RL, S.