Flanks of end mills are prone to wear in a long machining process. Regrinding is widely used in workshops to restore the flank to an original-like state. However, the traditional method involves material waste by trial and error and dramatically decreases the potential regrinding. Moreover, over-cut would happen to the flutes of worn cutters in the regrinding processes because of improper wheel path. This study presented a new approach to planning the wheel path for regrinding worn end mills to minimize material loss and recover the over-cut. In planning, a scaling method was developed to determine the maximum size of the new cutter according to the similarity of cutter shapes before and after regrinding. Then, the wheel path is first generated by envelope theory to regrind the worn area with a four-axis computer numerical control grinder according to the new size of cutters. Moreover, a second regrinding strategy is applied to recover the flute shape over-cut in the first grinding. Finally, the proposed method is verified by an experiment. Results showed that the proposed approach could save 25% of cutter material compared with the traditional method and ensure at least three regrinding times. This work effectively provides a general regrinding solution for the worn flank with maximum material-saving and regrinding period.