Hey, Rizz I appreciate your help, and to help a bit, I had tried tinkering with the trigger myself, and it sorta works...
Trigger:
Events:
Unit - A unit Is issued an order targeting a point
Conditions:
((Triggering Unit) has buff Trample ) Equal to True
Actions:
Set Trampler = Triggering Unit
Unit Group - Pick every unit in (Units within 75.00 of ((Positon of Trampler) offset by 35.00 towards 0.00 degrees)) and do (Actions)
Loop - Actions
If (All Conditions are True) then do (Then Actions) else do (Else Actions)
If - Conditions
((Owner of Picked Unit)) is an enemy of (Owner of Trampler)) Equal to True
((Picked Unit) is alive) Equal to True
Then - Actions
Unit - Cause Trampler to damage (Picked unit), dealing 5.00 damage of attack type Normal and damage type Normal
....only problem with this is that it only tramples units that are within the position of trampler 35 units to the right (X Axis). Possibly if we're able to constantly update the trampler's positon so that it always tramples what is front of him, maybe it could work?