The only race Uncle Jessie and Boss had was a rematch moonshine run called "Days of Shine and Roses" season 2. Where they watched an old clip of their old run shine days. After the film, boss got bragging about being the best until Bo put his 2 cents worth, which led to the moon shine run between two old moonshine runners. Season 6, "Boss Behind Bars", also another race with Boss and Jessie in it, where the beaudries sabataged jessies car and pin it on Boss, so boss had to go to jail for causin Jessie accident. the scene is "The Boar's Nest Bears", where kids play basket ball where Boss and tate have a bet on who will win. with the help of dukes and moffet, boss wins and collects money from tate. But before Boss could do anything, Jessie hollored on the mic and announced that boss was gona donate $10,000 ....