I have a bunch of self extracting .EXE files that I'm using 7-Zip to extract. I only want files to be overwritten with newer versions. The 7-Zip extract dialog only gives me the option to overwrite files without asking, not about which file wins. The dialog seems to imply that the newly extracted file will always overwrite the existing file, regardless of timestamp.
I doubt that any of the sfx front ends allow for this. You'll probably have to use the archive's extraction utility to do this. 7-zip does have some alternate sfx modules available from it's SourceForge project page, maybe one of those will give you that feature.