The stock pump is for "one way" (pressure lift, gravity drop) hydraulic operation only.
It MIGHT lift your drill if you connect it like this: Connect the hose from the blind end of the cylinder to the front port on the right side of the tractor. Then remove the hose from the rod end of the cylinder and replace it with an air strainer fitting. However the pump may not have the pressure and oil capacity to fully extend the cylinder under load.
A better alternative is to install a 4-way hydraulic spool valve. Supply it from the same pump port as above, and plumb the return line back to the dipstick tube. You will now have 2-way (power in both directions) hydraulics.
However depending on the condition of the pump you still may not have sufficient pressure to lift your drill.
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