$re = '/(\n\n)-\s*(?!.*(?:(?<!-)\n-|\n-))/m';
$str = 'Here are few example strings where a leading dash character should be removed (note newlines):
- Lovely day.
- Lovely day-night cycle.
- Lovely day.
Isn\'t it?
- lovely day - isn\'t it?
- Lovely day -
isn\'t it?
Here are few example strings where leading dash character(s) should be retained (note the 2nd example, it might be tricky):
- Lovely day.
- Yeah, isn\'t it?
Lovely day.
- Yeah, isn\'t it?
- lovely day - isn\'t it?
- Yes.
- Lovely day for a -
- Walk?
';
$subst = "$1";
$result = preg_replace($re, $subst, $str);
echo "The result of the substitution is ".$result;
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for PHP, please visit: http://php.net/manual/en/ref.pcre.php