Abstract: A die handle oiling system for use with a cutting die head comprising a tubular handle having a sealed base end, a sealed tip end adapted for holding a cutting die head thereon, an air cavity for holding air formed therein adjacent to the base end, a plunger cavity for holding oil formed therein adjacent to the tip end and in communication with the air cavity, an inlet valve extended from the air cavity for allowing air to be disposed therein, a pressure release valve extended from the air cavity for allowing air to be released therefrom, a sealable filling bore extended from the plunger cavity for allowing oil to be disposed therein, and an oil outlet extended from the plunger for allowing oil to be released therefrom; a plunger slidably disposed within the plunger cavity; an oil hose coupled to the oil outlet; and an actuatable air pump coupled to the inlet valve for filling the air cavity with air; whereby when the air pump is actuated, air pressure builds in the air cavity and forces the plunger towards t