Popsugar Entertainment Dancing With The Stars Who Has Won Dancing With the Stars? All 29 Celebrities Who Have Won Dancing With the Stars November 24, 2020 by Kelsie Gibson View On One Page Photo 11 of 30 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 11 Season 11: Jennifer Grey Partner: Derek Hough Runner-up: Kyle Massey Previous Next Start Slideshow Dancing With The StarsFall TVTVReality TV