Homeschool Winner is an early, obscure Homestar Runner character who was retired early on by the site's creators, Matt and Mike Chapman. The Homestar Runner fan following first discovered this character in one of the backgrounds of the Dancin' Bubs game, alongside another early character, a medal-wearing girl of name unknown. Later, someone discovered an unused .swf file on the Homestar Runner server (only one such file of many) that contained the pictures and names of not only all of the main characters, but also both the mysterious character, now known as Homeschool Winner, and a group of identical, creepy-looking creatures called the Unguraits. This file has since been deleted, but it has been archived on the fansite

Visually, Homeschool is skinnier than Homestar (although his relative height can only be guessed), his head is not as wide and hatless, he has an overbite (as opposed to Homestar's underbite), his shirt is blue, and the white symbol on his chest is a speech bubble instead of a star.

Homeschool Winner's original voice and personality are completely unknown at this time. It has been thought that Homseschool was intended to be a Bizarro-Homestar. If so, Homeschool has no place in the current Homestar Runner universe, as that position has already been taken up by Homsar.