The purpose of this study was to mechanize the task of planting chrysanthemum cuttings in plug trays. Seedling production using these trays is common in Japan to produce high-quality chrysanthemums, other flowers, and vegetables. However, chrysanthemum cuttings must be planted manually, which takes considerable time. Two models of planting machines suitable for chrysanthemum cuttings have been developed: a standard model for cuttings with no lower leaves, and a model that automatically removes the lower leaves. Both models are semi-automatic and employ a mechanism using rotating cups to facilitate a supply task of an operator and let two operators work side by side. In our laboratory and field experiments, the standard model had a failure rate of 0.5-3.1% and increased the maximum work efficiency to 2.4 times that of manual planting. The model that removed lower leaves had a failure rate of 0.8-4.5%, but also increased maximum work efficiency to 2.4 times that of manual planting. Although both models are influenced by individual supply variations from the workers, we believe they are ready for commercial use.