Thanks, the screenshots together with that description made the problem much clearer. This new macro I tried putting together isn't foolproof, but it might get you most of the way there, especially once you've put in the images you're using and adjusted the matching fuzziness:
Example Macro.kmmacros (653.4 KB)
The idea is to use the two For Each actions to scan the screen from top to bottom for matching images, then stop after the first match and save that match's screen coordinates to a variable. If both images are on the screen, it should use their corresponding variables to compare their Y coordinate values and click on the one that's lower (i.e. closer to the the top). Again, you'll probably need to tweak and adjust this to get it to where you want, and even then it might not get you all the way there, but it should hopefully be a start.