Guest Stars Timothy Granaderos as Montgomery De La Cruz Steven Weber as Principal Gary Bolan RJ Brown as Caleb Bryce Cass as Cyrus 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 Chelsea Alden as Mackenzie Allison Miller as Sonya Struhl Samantha Logan as Nina Jones Kelli O'Hara as Jackie Tom Everett Scott as Mr. Down Maria Dizzia as Mrs. Down Ben Lawson as Coach Rick Wlodimierz Makenzie Vega as Sarah Carlin Co Starring Brandon Butler as Scott Reed Keon Motakhaveri as Chad Moore Mason Guccione as Toby Fletcher Joey Chacho as Ramón Ordoñez Spence Moore II as Michael Jeanette Pavini as Maureen Carlin
