Look at you center photo of the door parts. On the left side, in the middle, is the front upper stop detail. It is a 'pressed' sheet metal bracket about the size of your thumb and has a bend in the center. It is bolted to the lower window frame and sticks out toward the inside of the door. When the window is rolled up it catches on a portion of the vent window/front runner frame that sticks straight back and is the size of about 2 fingers. You can see it if you look down the front channel with the window down.
This up stop may be adjusted to high and engaging before the window is in place.
When rolling up the window, is it level, then hits one stop before the other?
Your drawing also shows the rear up stop detail at the top right. A cast thing that looks like a wide J.
The photos are of my '66, but same idea.