Plunge milling is among the most effective methods of deep core/cavity shaped rough machining techniques. Previous research work had not considered the optimization of plunger selection and toolpoint path. In this paper a new method is proposed (overlapped circles filling (Ocfill)) for optimizing the selection of plungers and toolpoint path generation. The proposed method is used to fill 2D area with a number of overlapped circles. The 2D area is expressed as the feature that being cutting with plunge milling and the circles are plunging holes. The Ocfill method has been implemented in Visual C++. The Ocfill is applied to many examples. The results show that, Ocfill saves rough machining time by significant value up to 28%. This value depends on the shape and complexity of the workpiece that is being cut.