Nothing has been smooth for the 26-year-old since his first brush with the UFC back in August 2017. Simon was given a shot to earn a UFC contract on Dana White’s Tuesday Night Contender Series, but his split decision win over Donavon Frelow wasn’t enough to convince the boss to offer him a deal, so he ended up taking a couple of fights on the regional scene and capturing the Legacy Fighting Alliance bantamweight title before getting the short-notice call to fight Merab Dvalishvili at UFC Atlantic City.