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Best way is to do a count before insertion.

 

IE:

<?php
$count = mysql_fetch_assoc(mysql_query("SELECT count(gbid) count FROM guest_book;"));
$count = $count['count'];

if ($count > 100) {
      mysql_query("DELETE FROM guest_book ORDER BY dateentered LIMIT 1;");
}
?>

 

Note unsure if it works correctly test it on a dev machine before using it in production.

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