I'm not familiar with list compare, so it's possible there's something wrong with the syntax you're using, but the item that I noticed is that you're returning 0 within the loop.

Normally, you'd want to use logic like:

sub test_match_subroutine {
    my ( $item, $possible_matches ) = @_;
    foreach my $test_case ( @$possible_matches ) {
        return 1 if is_a_match($item, $test_case);
    }
    return 0;
}
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Note -- we don't fail until all cases fail ... not when the first item fails.