A pressure sensitive labeling machine incorporating a wedge shaped suction plate assembly which uses negative pressure to assist in securing and holding the non-adhesive side of a label carrier web. The labeling machine advances the label carrier web by automatically engaging and disengaging a pinch roller assembly driven by a pneumatic piston. The pinch roller assembly obviates the need for high maintenance clutching mechanisms and multiple tension roller assemblies. A label application station applies labels to passing containers when the carrier web advances around a label separator edge of the suction plate assembly by peeling the labels from the carrier web and applying the labels via a rotating applicator roller and container catch arm.