Abstract: A system for labeling a plurality of items, each having a periphery. The system has: a rotary-station comprising a pair of plate-members each having a rotation axis, the pair of plate-members is adapted for holding each of the plurality of items, individually; a labeler assembly for providing a plurality of dedicated labeling; a mechanism for applying a labeling-edge of a dedicated labeling created for a first item of the plurality of items, leaving a first labeling tail, while holding the first item between the pair of plate-members; and a roller for contouring the first labeling tail around at least a portion of the periphery of the first item by making contact between a rolling surface and the first labeling tail while the first item moves in a spinning fashion between the pair of plate-members. The system may incorporate a single-rotary station unit or a multi-rotary station unit. An associated method of labeling a plurality of items is also disclosed.