2010
Princess Abby, a chihuahua with "a hunched and peculiar walk due to that her back legs are longer than her front (which allows her to have moments of bipedalism), a missing eye, and mismatched ears", won the 2010 contest out of a field of 25 dogs. Despite being a rescue dog, she was entered in the pedigree division.
Read more about this topic: World's Ugliest Dog Contest