Background: Hickenbottom was born on July 22, 1965 in Chandler, Arizona. The last of four children - Randy, Scott, and Shari are his older siblings - he was raised in a military family and spent a brief part of his early years in Reading, Berkshire, England, but grew up in San Antonio, Texas. As a child, Hickenbottom disliked the name Michael, so his family and friends just called him Shawn. Ever since, he has been referred to as Shawn.
Context: On the December 14 Raw, Michaels won the Slammy Award for Moment of the Year for his match against The Undertaker at WrestleMania XXVI. Michaels accepted the award via satellite. Three days later, he announced a long-term deal with WWE, where he will serve in an ambassadorial role. He made his in-person TV return at the December 11 Tribute to the Troops taping, where he and Triple H had a one-night only DX reunion.  He appeared on the January 10, 2011 Raw, where he was announced as a WWE Hall of Fame class of 2011 inductee. After being ridiculed by Alberto Del Rio later that night, Michaels hit him with Sweet Chin Music. On the March 28 Raw, Michaels addressed Triple H and The Undertaker about their match at WrestleMania XXVII. Michaels was inducted into the WWE Hall of Fame on April 2 by Triple H. They were also joined by fellow Kliq members Kevin Nash (who had returned to WWE for the Royal Rumble) and Sean Waltman. He returned on the June 27 Raw, where he was confronted by CM Punk, and superkicked David Otunga and Michael McGillicutty. Later that night, when Diamond Dallas Page's special appearance was interrupted by Drew McIntyre, he superkicked McIntyre.  In June 2011, Jim Ross, Michaels and Hart announced that the three were working on a DVD chronicling the careers of Hart and Michaels that the WWE was planning to release in October 2011. The subject of the DVD would be their on-screen rivalry and real-life conflicts, with a particular focus on the Montreal screwjob. In his tweet, Hart described working on the DVD as a "cathartic" experience, and Ross asserted that both Hart and Michaels had been very honest and emotional in their interviews. The DVD, Shawn Michaels vs Bret Hart: WWE's Greatest Rivalries, was released in November 2011.
Question: When did he win it?

Answer:
December 14