Please read the following table in HTML format from a webpage and then answer the question in detail according to the table. Each table cell is defined by a <td> and a </td> tag. Each table row starts with a <tr> and ends with a </tr> tag. 'rowspan=m' and 'colspan=n' represents a cell spaning over 'm' rows and 'n' columns.

Webpage title:
Demus 3:16
Table title:
Luchas de Apuestas record
Table:
<table id='hittask' contenteditable='False'>
<tr> <th colspan=1 rowspan=1 > Winner (wager) </th><th colspan=1 rowspan=1 > Loser (wager) </th><th colspan=1 rowspan=1 > Location </th><th colspan=1 rowspan=1 > Event </th><th colspan=1 rowspan=1 > Date </th><th colspan=1 rowspan=1 > Notes </th></tr>
<tr> <td colspan=1 rowspan=1 > Bam Bam (hair) </td><td class="highlighted"  colspan=1 rowspan=1 > Pequeño Damián 666 (hair) </td><td colspan=1 rowspan=1 > Mexico City, Mexico </td><td colspan=1 rowspan=1 > Live event </td><td colspan=1 rowspan=1 > July 24, 2007 </td><td colspan=1 rowspan=1 >  </td></tr>
<tr> <td colspan=1 rowspan=1 > Pequeño Damián 666 (hair) </td><td colspan=1 rowspan=1 > Toshiya Matsuzaki (hair) </td><td colspan=1 rowspan=1 > Mexico City, Mexico </td><td colspan=1 rowspan=1 > DragonMania III </td><td colspan=1 rowspan=1 > May 11, 2008 </td><td colspan=1 rowspan=1 >  </td></tr>
<tr> <td colspan=1 rowspan=1 > Pequeño Damián 666 (hair) </td><td colspan=1 rowspan=1 > Bam Bam (hair) </td><td colspan=1 rowspan=1 > Mexico City, Mexico </td><td colspan=1 rowspan=1 > Live event </td><td colspan=1 rowspan=1 > August 17, 2008 </td><td colspan=1 rowspan=1 >  </td></tr>
<tr> <td class="highlighted"  colspan=1 rowspan=1 > Shockercito (hair) </td><td class="highlighted"  colspan=1 rowspan=1 > Pequeño Damián 666 (hair) </td><td colspan=1 rowspan=1 > Mexico City, Mexico </td><td colspan=1 rowspan=1 > Live event </td><td class="highlighted"  colspan=1 rowspan=1 > June 2, 2009 </td><td colspan=1 rowspan=1 >  </td></tr>
<tr> <td colspan=1 rowspan=1 > Pequeño Damián 666 (hair) </td><td colspan=1 rowspan=1 > Yaruba (hair) </td><td colspan=1 rowspan=1 > Mexico City, Mexico </td><td colspan=1 rowspan=1 > DragonMania V </td><td colspan=1 rowspan=1 > May 29, 2010 </td><td colspan=1 rowspan=1 >  </td></tr>
<tr> <td colspan=1 rowspan=1 > Demus 3:16 (hair) </td><td colspan=1 rowspan=1 > Bam Bam (hair) </td><td colspan=1 rowspan=1 > Mexico City, Mexico </td><td colspan=1 rowspan=1 > Live event </td><td colspan=1 rowspan=1 > July 6, 2010 </td><td colspan=1 rowspan=1 >  </td></tr>
<tr> <td colspan=1 rowspan=1 > Virus (hair, leadership) </td><td colspan=1 rowspan=1 > Demus 3:16 (hair, division) </td><td colspan=1 rowspan=1 > Mexico City, Mexico </td><td colspan=1 rowspan=1 > Live event </td><td colspan=1 rowspan=1 > March 11, 2011 </td><td colspan=1 rowspan=1 >  </td></tr>
<tr> <td colspan=1 rowspan=1 > Demus 3:16 (hair) </td><td colspan=1 rowspan=1 > Pequeño Black Warrior (hair) </td><td colspan=1 rowspan=1 > Mexico City, Mexico </td><td colspan=1 rowspan=1 > Live event </td><td colspan=1 rowspan=1 > September 18, 2011 </td><td colspan=1 rowspan=1 >  </td></tr>
<tr> <td colspan=1 rowspan=1 > Shockercito (hair) </td><td colspan=1 rowspan=1 > Demus 3:16 (hair) </td><td colspan=1 rowspan=1 > Mexico City, Mexico </td><td colspan=1 rowspan=1 > Live event </td><td colspan=1 rowspan=1 > October 16, 2015 </td><td colspan=1 rowspan=1 >  </td></tr>
<tr> <td colspan=1 rowspan=1 > Wotan (hair) </td><td colspan=1 rowspan=1 > Demus 3:16 (beard) </td><td colspan=1 rowspan=1 > Irapuato, Guanajuato, Mexico </td><td colspan=1 rowspan=1 > Live event </td><td colspan=1 rowspan=1 > December 18, 2017 </td><td colspan=1 rowspan=1 >  </td></tr>
<tr> <td colspan=1 rowspan=1 > Demus (hair) </td><td colspan=1 rowspan=1 > Dragoncito de Oro (mask) </td><td colspan=1 rowspan=1 > Tlalnepantla, State of Mexico </td><td colspan=1 rowspan=1 > Lucha Libre Boom show </td><td colspan=1 rowspan=1 > October 7, 2018 </td><td colspan=1 rowspan=1 >  </td></tr>
<tr> <td colspan=1 rowspan=1 > Demus (hair) </td><td colspan=1 rowspan=1 > Gato de Ecatepec (mask) </td><td colspan=1 rowspan=1 >  </td><td colspan=1 rowspan=1 > Lucha Memes Chairo Kingdom </td><td colspan=1 rowspan=1 > March 31, 2019 </td><td colspan=1 rowspan=1 >  </td></tr>
</table>
Question:
When was the second time that Pequeño Damián lost his hair?
Answer:
On June 2, 2009, Pequeño Damián 666 lost a Luchas de Apuetas match to Shockercito, losing his hair for the second time in his career.