Guest Stars Timothy Granaderos as Montgomery De La Cruz Josh Hamilton as Matt Jensen Michele Selene Ang as Courtney Crimsen Bryce Cass as Cyrus RJ Brown as Caleb Joseph C. Phillips as Greg Davis Anne Winters as Chlöe Rice Wilson Cruz as Dennis Vasquez Ajiona Alexus as Sheri Holland Steven Silver as Marcus Cole Samantha Logan as Nina Jones Allison Miller as Sonya Struhl Sosie Bacon as Skye Miller Kelli O'Hara as Jackie Cindy Cheung as Karen Dempsey Tom Everett Scott as Mr. Down Andrea Roth as Noelle Davis Ben Lawson as Coach Rick Wlodimierz Robert Gant as Todd Crimsen Alex Quijano as Steve Crimsen Co Starring Brandon Butler as Scott Reed Richard Gross as Judge Campbell Joey Chacho as Ramón Ordoñez Mikiko Edwards as Cheerleader #1 Callan Taylor as Cheerleader #2