 <p><code>match</code> accept regex for <code>url</code> value. Try:</p> <pre><code>&lt;match url="(.*?)/?awards?(\.aspx)?$" /&gt; </code></pre> <p><a href="https://www.debuggex.com/r/flpHf1GKQeQcdYCo" rel="nofollow"><img src="https://www.debuggex.com/i/7YkHJSHFyJDwo-99.png" alt="Regular expression visualization"></a></p> <p>This will match <code>award</code>, <code>award.aspx</code>, <code>awards</code> and <code>awards.aspx</code>.</p> <p><strong>Update</strong> to match <code>/test</code> as well:</p> <pre><code>&lt;match url="(.*?)/?(awards?|test)(\.aspx)?$" /&gt; </code></pre> <p><a href="https://www.debuggex.com/r/ht3kA7il9EtWmIdn" rel="nofollow"><img src="https://www.debuggex.com/i/ApnzxG8guGJkFLyV.png" alt="Regular expression visualization"></a></p> <p>It is just a <a href="http://www.regular-expressions.info/" rel="nofollow">regular expression</a>. You can match whatever you want.</p>