Okay, now remove the 4 top roller track screws so that you can manually move the glass to the fully up position, free of interference from being connected to the window regulator. This will let you know if the glass fits the hole.
If it fits nicely all the way up, then roll the regulator all the way up to see if it reaches up far enough to do what it is supposed to do. If not, then you will now know where the problem is. The regulator has a hitch in its get along. Maybe a bend gear tooth, or a bad upper or lower track roller.
