$re = '/<b>(?:(?!<\/?b>).)*?<\/b>(?:(?!<\/?b>).)*?<font color=darkslategray>.*?<\/font>/i';
$str = 'naive
<b>na·ive</b><br><div style="padding-left:0.5em;">(<VR><span style="color:#006400;font-style:italic">or</span> <b>na·ïve</b></VR>) <font color=darkslategray>/nɑˈiːv, naıˈiːv/</font> <span style="color:#006400;font-style:italic">adj</span> [<i>more ~; most ~</i>]<br></div><div style="padding-left:1em;"><b>:</b> having or showing a lack of experience or knowledge <b>:</b> innocent or simple<br></div><div style="padding-left:1.5em;"><font color="#004A95">a <i>naive</i> belief that all people are good</font><br></div><div style="padding-left:1.5em;"><font color="#004A95">a <i>naive</i> view of the world</font><br></div><div style="padding-left:1.5em;"><font color="#004A95">I <i>naively</i> believed that we could fix the problem.</font><br></div><div style="padding-left:1em;"><b>na·ïve·té</b> (<VR><span style="color:#006400;font-style:italic">also</span> <b>na·ive·te</b> <span style="color:#006400;font-style:italic">or</span> <b>na·ive·té</b></VR>) <font color=darkslategray>/nɑˌiːvˈteı, naıˌiːvˈteı/</font> <span style="color:#006400;font-style:italic">noun</span> [<span style="color:#006400;font-style:italic">noncount</span>]<br></div><div style="padding-left:1.5em;"><font color="#004A95">political <i>naïveté</i></font><br></div><div style="padding-left:1em;"><b>na·ive·ty</b> (<VR><span style="color:#006400;font-style:italic">also</span> <b>na·ïve·ty</b></VR>) <font color=darkslategray>/nɑˈiːvəti, naıˈiːvəti/</font> <span style="color:#006400;font-style:italic">noun</span> [<span style="color:#006400;font-style:italic">noncount</span>] <span style="color:#006400;font-style:italic">chiefly Brit</span><br></div><div style="padding-left:1.5em;"><font color="#004A95">political <i>naïvety</i></font><br></div>';
preg_match_all($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