I'm not sure this silly question about a silly game is worth continuing to hash out, but . . . If the sphere stops energy from going through either way, how will the energy of the fall get inside?
Short answer? Magic.
My long answer:
Basic laws of motion: a boulder transfers momentum to the ground when it hits. There is an equal and opposite reaction. Energy is introduced into the equation by the momentum of the boulder striking the ground which pushes back with equal force.
However, we have a sphere that is weightless so therefore has no mass. It cannot have momentum because momentum = mass X velocity.
When the sphere falls off the edge of the cliff, the sphere does not technically fall (it has no mass and is unaffected by gravitational force). It is pushed by the occupant. The occupant accelerates towards the ground as normal because gravity sucks and it's been stated that the occupant can move the sphere.
The occupant of the sphere does not hit the ground. The sphere hits the ground, but it has no momentum so it does not transfer any momentum to the ground. There is no equal and opposite reaction because no momentum was transferred. It's velocity still becomes zero relative to the ground. Because
magic.
The occupant still has momentum so they hit interior of the sphere. They cannot transfer momentum to the sphere, there can be no equal and opposite reaction in the standard Newtonian sense. They stop because
magic.
If their velocity was high enough when they stop, and the stop is sudden enough they take damage. The damage does not originate from outside of the sphere - it happens because of the occupant's sudden deceleration caused by the magic of the sphere and the occupant's momentum.
There are all sorts of issues with ORS if you say you cannot transfer any energy from the exterior to the interior - basically the occupant would never gain momentum (change their velocity). You could not move the sphere because you could not move the occupant. Unless magic. If magic gives the occupant velocity, then magic can take reduce relative velocity to zero.
Or the occupant becomes effectively weightless (and massless) in which case all of the issues go away. You could even decide that the sphere offers no air resistance, since air is the one thing that can pass through the sphere. That also means that while you could pick up and carry the sphere, you could not throw it.