slowgoer,
I'm not a transmission guru by any means, but the cutaway of this box does appear to have that hole pointed down...directly at the ground. There is no seal, there is a oil slinger immediately in back of the bearing that keeps oil from running out the clutch gear when the rig is running.
If the transmission is overfilled, or the truck is parked on a VERY steep incline, nose down, it can leak.
Stuart