Guest Stars Timothy Granaderos as Montgomery De La Cruz Josh Hamilton as Matt Jensen Bryce Cass as Cyrus RJ Brown as Caleb Brenda Strong as Nora Walker Joseph C. Phillips as Greg Davis Anne Winters as Chlöe Rice Wilson Cruz as Dennis Vasquez Ajiona Alexus as Sheri Holland Tommy Dorfman as Ryan Shaver Samantha Logan as Nina Jones Allison Miller as Sonya Struhl Kelli O'Hara as Jackie Cindy Cheung as Karen Dempsey Matthew Alan as Seth Maria Dizzia as Mrs. Down Jake Weber as Barry Walker Ben Lawson as Coach Rick Wlodimierz Jackie Geary as Amber Foley Brittany Perry-Russell as Dre Porter Co Starring Keon Motakhaveri as Chad Moore Richard Gross as Judge Campbell Mikiko Edwards as Cheerleader #1 Irina Voronina as Ivanka