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It isn't a list nor an array in scalar context that your example is making use of. It is a list assignment (in scalar context).
A list assignment in scalar context returns the number of items in the right-hand list.
And, in your example, 'x' =~ m/(.)(.)/, in a list context, returns an empty list, not a list of two 'undef's. An empty list (on the right-hand side of the list assignment) contains zero items so the assignment in scalar context returns 0, which is one of the documented false values.
But there is a kernel of truth hidden behind your mistakes.
There have been some exceptions (as near as I can remember, on an inconsistent basis) to the rule about what a list assignment returns in scalar context. Those exceptions were meant to handle cases very similar to what you described.
In some versions of Perl, that code would print "false". In the relatively modern Perl I had handy, it prints "true".
I even recall having a very short on-line conversation with Larry years ago about what I considered to be bugs such as ( undef, undef ) being an empty list instead of being a list containing a single 'undef' and he was worried about breaking the fact that the above code was supposed to print "false". I argued that that wasn't a feature worth keeping.
But I didn't follow-up to see what decisions were made back then. And, just now, I didn't test the current behavior except minimally. I think there was at least one thread about this stuff on PerlMonks around the time Larry and I talked, but I haven't looked for it. It might've just been in the chatterbox.
In reply to Re^3: What is true and false in Perl? (undef,undef)