$re = '/^\h*#\h*(2020.*)([\s\S]*?(?:(?=(^\h*#\h*2020.*))|\z))/m';
$str = '# Title
# 2020-01-01
Multi-line content
goes here
# 2020-01-02
Other multi-line content
goes here';
preg_match_all($re, $str, $matches, PREG_SET_ORDER, 0);
// Print the entire match result
var_dump($matches);
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