In my opinion, the main difference is that I can't imagine a native speaker using the first one. I'd use either the second or "It's likely I wouldn't have understood him".
In one of my previous posts you revised my question to read as follows: "To be frank, if there were no subtitles,
I would be unlikely to have understood him. Might be The context
would might have help
ed me somehow.
It represents It's a problem for me. I was trying to find
a kind other examples/instances of his
American pronunciation of "needed" in You
Tube and You
Glish but failed." Can you please clarify whether such construction as " I would
be unlikely
to have understood him" is Okay from grammatical point of view, but nevertheless is considered to be unconventional for English speakers?