Loosen the powder measure and back it out of the bushing. Then with a case properly trimmed to the "trim to" length, screw in the powder measure until the drum is at the top of the stroke for dumping powder. Tighten the lock nut at this location and your measure will be set up properly for that length of case.
Due to the different amounts the case mouths have been collapsed, I would guess that this brass hadn't been trimmed before being loaded. Either that, or you just stopped the press stroke at different places.
At any rate, your powder measure isn't adjusted properly, and correcting that will solve your problem.
Hope this helps.
Fred